You are on page 1of 64

SciFinder Page 1

Task History

Task Began September 10, 2017 08:48 AM


Explore substances by SUBSTRUCTURE ID(2)

Answer Type: Substances


Result Count: 81
Retrieve reference information in 1 substance (ID 6)
From ID: 2
Answer Type: References
Result Count: 18
SciFinder Page 2
1. Bis(aminomethyl)phosphinic Acid, a Highly Promising Scaffold for the Development of Bacterial Urease
Inhibitors
By: Macegoniuk, Katarzyna; Dzielak, Anna; Mucha, Artur; Berlicki, Lukasz

Source: ACS Medicinal Chemistry Letters, Volume: 6, Issue: 2, Pages: 146-150, Journal; Online Computer File, 2015, CODEN: AMCLCT,
ISSN: 1948-5875, DOI: 10.1021/ml500380f

Company/Organization: Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wroclaw, Pol., 50-370

Accession Number: 2014:2082008, CAN 162:230275, CAPLUS


Publisher: American Chemical Society
Language: English

Abstract
Inhibitors of bacterial ureases are considered to be promising compds. in the treatment of infections caused by
Helicobacter pylori in the gastric tract and/or by urealytic bacteria (e.g., Proteus species) in the urinary tract. A new,
extended transition state scaffold, bis(aminomethyl)phosphinic acid, was successfully explored for the construction of
effective enzyme inhibitors. A reliable methodol. for the synthesis of phosphinate analogs in a three-component
Mannich-type reaction was elaborated. The obtained mols. were assayed against ureases purified from Sporosarcina
pasteurii and Proteus mirabilis, and aminomethyl(N-n-hexylaminomethyl)phosphinic acid was found to be the most potent
inhibitor, with a Ki = 108 nM against the S. pasteurii enzyme.

Indexing
Enzymes (Section 7-3)
Concepts
Enzyme functional sites
active; bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development
of bacterial urease inhibitors
Enzyme inhibition kinetics
Molecular association
Molecular recognition
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
Structure-activity relationship
enzyme-inhibiting; bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for
development of bacterial urease inhibitors
C-P bond
stability; bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development
of bacterial urease inhibitors
Substances
9002-13-5 Urease

bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
SciFinder Page 3
Biological study, unclassified; Properties; Biological study
1643319-10-1P

bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors

Biological study, unclassified; Properties; Reactant; Synthetic preparation; Biological study; Preparation; Reactant or
reagent
127590-10-7P
1643318-96-0P
1643318-97-1P
1643318-98-2P
1643318-99-3P
1643319-00-9P
1643319-01-0P
1643319-02-1P
1643319-03-2P
1643319-04-3P
1643319-05-4P
1643319-06-5P
1643319-07-6P
1643319-08-7P
1643319-09-8P
1643319-11-2P

bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors

Biological study, unclassified; Properties; Synthetic preparation; Biological study; Preparation


1239975-64-4P
1643319-12-3P

bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors

Byproduct; Preparation
1643319-14-5P
1643319-15-6P
SciFinder Page 4
1643319-16-7P
1643319-17-8P
1643319-18-9P
1643319-19-0P
1643319-20-3P
1643319-21-4P
1643319-22-5P
1643319-23-6P
1643319-24-7P
1643319-25-8P

bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors

Properties; Reactant; Synthetic preparation; Preparation; Reactant or reagent

50-00-0 Formaldehyde, reactions


100-46-9 Benzylamine, reactions
103-67-3 N-Methylbenzylamine
109-89-7 Diethylamine, reactions
110-89-4 Piperidine, reactions
124-40-3 Dimethylamine, reactions
1667-16-9 N-Octylbenzylamine
2032-33-9 N-Propylbenzylamine
2403-22-7 N-Butylbenzylamine
4383-25-9 N-Cyclohexylbenzylamine
5730-02-9 N-Heptylbenzylamine
6303-21-5 Hypophosphorous acid
13274-83-4 Bis(chloromethyl)phosphinic acid
25468-43-3 N-Pentylbenzylamine
25468-44-4 N-Hexylbenzylamine
42882-36-0 N-Iso-Butylbenzylamine
131066-43-8

bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors

Reactant; Reactant or reagent


1643319-13-4P

bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors

Reactant; Synthetic preparation; Preparation; Reactant or reagent


Supplementary Terms
bis aminomethylphosphinate prepn extended transition state scaffold inhibitor urease
Citations
SciFinder Page 5
1)Amtul, Z; Curr Med Chem 2002, 9, 1323
2)Ashiralieva, A; FEBS Lett 2003, 555, 367
3)Bailie, N; Am J Vet Res 1986, 47, 2604
4)Baylis, E; J Chem Soc, Perkin Trans 1 1984, 2845
5)Benini, S; J Biol Inorg Chem 1998, 3, 268
6)Berlicki, L; Amino Acids 2012, 42, 1937
7)Bichler, K; Int J Antimicrob Agents 2002, 19, 488
8)Dixon, N; J Am Chem Soc 1975, 97, 4130
9)Dzielak, A; Tetrahedron Lett 2011, 52, 3141
10)Eaton, K; Infect Immun 1991, 59, 2470
11)Faraci, W; Bioorg Med Chem 1995, 3, 605
12)Fishbein, W; J Biol Chem 1965, 240, 2407
13)Follmer, C; J Clin Pathol 2010, 63, 424
14)Griffith, D; Eur Urol 1991, 20, 243
15)Griffith, D; Urol Res 1979, 7, 215
16)Hase, J; J Biochem 1967, 62, 293
17)Ikeda, S; J Am Chem Soc 1992, 114, 7604
18)Karplus, P; Acc Chem Res 1997, 30, 330
19)Kobashi, K; Biochim Biophys Acta 1962, 65, 380
20)Kobashi, K; J Biochem 1985, 98, 1681
21)Kosikowska, P; Expert Opin Ther Pat 2011, 21, 945
22)Kot, M; J Enzyme Inhib Med Chem 2001, 16, 507
23)Krajewska, B; J Mol Catal B 2009, 59, 9
24)Maier, L; J Organomet Chem 1979, 178, 157
25)Miano, R; Urol Int 2007, 79, 32
26)Mobley, H; J Clin Microbiol 1987, 25, 2216
27)Mobley, H; Microbiol Rev 1995, 59, 451
28)Mucha, A; J Med Chem 2011, 54, 5955
29)Nicolle, L; Clin Microb News 2002, 24, 135
30)Pope, A; Dig Dis Sci 1998, 43, 109
31)Scott, D; Gastroenterology 1998, 114, 58
32)Shaw, W; J Am Chem Soc 1961, 83, 3184
33)Vassiliou, S; ARKIVOC 2012, iv, 33
34)Vassiliou, S; J Med Chem 2008, 51, 5736
35)Vassiliou, S; J Med Chem 2010, 53, 5597
36)Xiao, Z; Bioorg Med Chem 2007, 15, 3703
37)Xiao, Z; Eur J Med Chem 2010, 45, 5064
38)Zaborska, W; J Enzyme Inhib Med Chem 2002, 17, 247
39)Zaborska, W; J Mol Catal B 2001, 13, 103
40)Zhukov, Y; Mendeleev Commun 2004, 14, 93
Tags
0 Tags
Comments
0 Comments
Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

2. Metal complexes of a new class of polydentate Mannich bases: Synthesis and spectroscopic characterisation
By: Al-Jeboori, Mohamad J.; Al-Jebouri, Fahad A.; Al-Azzawi, Muayed A. R.

Source: Inorganica Chimica Acta, Volume: 379, Issue: 1, Pages: 163-170, Journal; Online Computer File, 2011, CODEN: ICHAA3, ISSN:
0020-1693, DOI: 10.1016/j.ica.2011.10.013
SciFinder Page 6
Company/Organization: Department of Chemistry, College of Education, Ibn Al-Haitham, University of Baghdad, Baghdad, Iraq

Accession Number: 2011:1493010, CAN 155:700634, CAPLUS


Publisher: Elsevier B.V.
Language: English

Abstract
A new class of polydentate Mannich bases featuring an N2S2 donor system, bis((2-mercapto-N-
phenylacetamido)methyl)phosphinic acid H3L1 and bis((2-mercapto-N-propylacetamido)methyl)phosphinic acid H3L2,
was synthesized from condensation of phosphinic acid and paraformaldehyde with 2-mercaptophenylacetamide W1 and
2-mercaptopropylacetamide W2, resp. Monomeric complexes of these ligands, K2[CrIII(Ln)Cl2], K3[M'II(Ln)Cl2] and
K[M(Ln)] (M' = Mn(II) or Fe(II); M = Co(II), Ni(II), Cu(II), Zn(II), Cd(II) or Hg(II); n = 1, 2) are reported. The structures of
new ligands, mode of bonding and overall geometry of the complexes were detd. through IR, UV-visible, NMR, and mass
spectral studies, magnetic moment measurements, elemental anal., metal content, and conductance. These studies
revealed octahedral geometries for the Cr(III), Mn(II) and Fe(II) complexes, square planar for Ni(II) and Cu(II) complexes
and tetrahedral for the Co(II), Zn(II), Cd(II) and Hg(II) complexes. Complex formation studies via molar ratio in DMF soln.
were consistent to those found in the solid complexes with a ratio of (M:L) as (1:1).
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
Transition metal complexes
prepn. of transition metal complexes of bis(mercaptoacetamide)phosphinic acid polydentate Mannich bases
Synthetic preparation; Preparation
Mannich bases
transition metal complexes; prepn. of transition metal complexes of bis(mercaptoacetamide)phosphinic acid polydentate
Mannich bases
Synthetic preparation; Preparation
Substances
62-53-3 Benzenamine, reactions
68-11-1 reactions
107-10-8 1-Propanamine, reactions
6303-21-5 Phosphinic acid
30525-89-4 Paraformaldehyde

prepn. of transition metal complexes of bis(mercaptoacetamide)phosphinic acid polydentate Mannich bases

Reactant; Reactant or reagent


4822-44-0P
38042-20-5P
1350518-13-6P
1350518-14-7P

prepn. of transition metal complexes of bis(mercaptoacetamide)phosphinic acid polydentate Mannich bases

Reactant; Synthetic preparation; Preparation; Reactant or reagent


1350517-94-0P
SciFinder Page 7

1350517-95-1P

1350517-97-3P
SciFinder Page 8

1350517-98-4P

1350517-99-5P
SciFinder Page 9

1350518-00-1P

1350518-01-2P
SciFinder Page 10

1350518-02-3P

1350518-03-4P
SciFinder Page 11

1350518-04-5P
1350518-05-6P
1350518-06-7P
1350518-07-8P
1350518-08-9P
1350518-09-0P
1350518-10-3P
1350518-11-4P
1350518-12-5P

prepn. of transition metal complexes of bis(mercaptoacetamide)phosphinic acid polydentate Mannich bases

Synthetic preparation; Preparation


Supplementary Terms
transition metal polydentate Mannich base complex prepn
Citations
1)Abdul-Ghani, A; J Coord Chem 2009, 62, 2736
2)Abram, U; Comprehensive Coordination Chemistry, second ed 2004
3)Abu-Hussen, A; J Coord Chem 2004, 57, 973
4)Ahsen, V; J Chem Soc, Dalton Trans 1987, 1827
5)Al-Jeboori, M; Global J Inorg Chem 2010, 1, 132
6)Al-Jeboori, M; Inorg Chim Acta 2010, 363, 1301
7)Al-Jeboori, M; J Ibn Al-Haitham Pure Appl Sci 2004, 17, 80
8)Al-Jeboori, M; Mu'tah Lil-Buhuth Wad-Dirasat 2003, 18, 83
9)Al-Jeboori, M; Transition Metal of Chemistry 2008, 33, 925
SciFinder Page 12
10)Baghiaf, A; Polyhedron 1985, 4, 853
11)Bartholoma, M; Chem Rev 2010, 110, 2903
12)Buchardt, J; Chem Eur J 1999, 5, 2877
13)Chandra, S; Spectrochim Acta, Part A 2008, 69, 1
14)Chen, H; J Med Chem 2000, 43, 1348
15)Chiang, C; J Biol Inorg Chem 2006, 11, 359
16)Diltz, S; Tetrahedron Asymmetr 1997, 8, 3559
17)Dilworth, J; Chem Soc Rev 1998, 27, 43
18)El-Asmy, A; Int J Pure Appl Chem 2006, 1, 75
19)Geary, W; Coord Chem Rev 1971, 7, 81
20)Groves, J; J Inorg Biochem 2006, 100, 434
21)Himes, R; Angew Chem, Int Ed 2010, 49, 6714
22)Kafarski, P; Aminophosphinic and aminophosphinic acids, chemistry and biological activity, first ed 2000
23)Kersemans, V; Pharmaceuticals 2010, 3, 600
24)Lee, D; Org Lett 2001, 3, 5
25)Lever, A; Inorganic Electronic Spectroscopy, second ed 1984
26)Liu, S; Chem Rev 1999, 99, 2235
27)Lukes, I; Dalton Trans 2007, 535
28)Moura, C; J Organomet Chem 2009, 694, 950
29)Nakamoto, K; Infrared Spectra of Inorganic and Coordination Compounds, fourth ed 1996
30)Nasman, O; Phosphorus, Sulfur, Silicon 2008, 183, 1541
31)Orvig, C; Inorg Chem 2002, 41, 685
32)Pellei, M; Curr Bioact Compd 2009, 5, 321
33)Raman, N; J Chem Sci 2004, 116, 209
34)Rampersad, M; Angew Chem, Int Ed 2005, 44, 1217
35)Rao, P; Chem Rev 2004, 104, 527
36)Reglinski, J; Curr Bioact Compd 2009, 5, 264
37)Sreedaran, S; Polyhedron 2008, 27, 2931
38)Sun, Y; J Med Chem 1996, 39, 458
39)Sutton, D; Electronic Spectra of Transition Metal Complex, first ed 1969
40)Tarafder, M; Polyhedron 2002, 27, 2683
41)Taylor, W; Can J Chem 1992, 70, 165
42)Tommasino, M; Tetrahedron Asymmetr 2000, 11, 4835
43)Wang, Y; J Chem Soc, Perkin Trans 1997, 2, 899
44)Weeks, A; Eur J Nucl Med Mol Imaging 2010, 37, 330
45)Yano, T; Eur J Inorg Chem 2006, 3753
46)Yousif, N; Synth React Inorg Met 2003, 33, 647
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

3. Synthesis and spectral studies of new N2S2 and N2O2 Mannich base ligands and their metal complexes
By: Abdul-Ghani, Ahlam Jamil; Al-Jeboori, Mohamad Jaber; Al-Karawi, Ahmed Jasim M.

Source: Journal of Coordination Chemistry, Volume: 62, Issue: 16, Pages: 2736-2744, Journal, 2009, CODEN: JCCMBQ, ISSN: 0095-
8972, DOI: 10.1080/00958970902878327

Company/Organization: Department of Chemistry, College of Sciences, University of Baghdad, Baghdad, Jaderiya, Iraq

Accession Number: 2009:877370, CAN 151:394616, CAPLUS


SciFinder Page 13
Publisher: Taylor & Francis Ltd.
Language: English

Abstract
The new Mannich bases dimethylphosphinic acid bis(thiosemicarbazide) (H3L1) and dimethylphosphinic acid bis(1-
phenylsemicarbazide) (H3L2) were synthesized from condensation of phosphinic acid and formaldehyde with
thiosemicarbazide and 1-phenylsemicarbazide, resp. Monomeric complexes of these ligands, K2[CrIII(Ln)Cl2],
K3[FeII(L1)Cl2], K3[MnII(L2)Cl2], and K[M(Ln)] (M = Co(II), Ni(II), Cu(II), Zn(II) or Cd(II); n = 1, 2) are reported. The mode
of bonding and overall geometry of the complexes were detd. through IR, UV-visible, NMR, and mass spectral studies,
magnetic moment measurements, elemental anal., metal content, and conductance. These studies revealed octahedral
geometries for the Cr(III), Mn(II), and Fe(II) complexes, square planar for Co(II), Ni(II), and Cu(II) complexes and
tetrahedral for the Zn(II) and Cd(II) complexes. Complex formation via molar ratio in DMF soln. was studied and results
were consistent to those found in the solid complexes with a ratio of (M:L) as (1:1).
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
IR spectra
UV and visible spectra
prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid
bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes
Transition metal complexes
prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid
bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes
Properties; Synthetic preparation; Preparation
Mannich bases
transition metal complexes; prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid
bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes
Properties; Synthetic preparation; Preparation
Substances
1187655-64-6P
1187655-65-7P
1187655-66-8P
1187655-67-9P
1187655-68-0P
1187655-69-1P
1187655-70-4P
1187655-71-5P
SciFinder Page 14

1187655-72-6P
SciFinder Page 15
1187655-73-7P

1187655-74-8P
SciFinder Page 16

1187655-75-9P
SciFinder Page 17
1187655-76-0P

prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid


bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes

Properties; Synthetic preparation; Preparation

50-00-0 Formaldehyde, reactions


79-19-6 Thiosemicarbazide
103-03-7 1-Phenylsemicarbazide
6303-21-5 Phosphinic acid

prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid


bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes

Reactant; Reactant or reagent


1187655-77-1P
1187655-78-2P

prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid


bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes

Reactant; Synthetic preparation; Preparation; Reactant or reagent


Supplementary Terms
transition metal dimethylphosphinic acid thiosemicarbazide phenylsemicarbazide Mannich complex prepn
Citations
SciFinder Page 18
1)Abu-Hussen, A; J Coord Chem 2004, 57, 973
2)Baghiaf, A; Polyhedron 1985, 4, 853
3)Birodar, N; Inorg Chem Acta 1976, 17, 157
4)Buchardt, J; Chem Eur J 1999, 5, 2877
5)Chen, H; J Med Chem 2000, 43, 1348
6)Chkaku, N; Inorg Chem 1971, 10, 768
7)El-Asmy, A; Int J Pure Appl Chem 2006, 1, 75
8)El-Asmy, A; J Coord Chem 2005, 58, 1735
9)El-Asmy, A; Trans Met Chem 1987, 12, 248
10)El-Metwally, N; Spectro Chem Acta 2005, 61, 1113
11)El-Shazly, R; Spectro Chim Acta 2005, 61, 243
12)El-said, F; Trans Met Chem 2003, 28, 954
13)Feedlander, B; J Am Chem Soc 1952, 18, 638
14)Figgis, B; Introduction to Ligand Field 1966
15)Geary, W; Coord Chem Rev 1971, 7, 81
16)Kabil, M; Anal Sci 1996, 12, 431
17)Kabil, M; J Anal Chem 1997, 357, 401
18)Kafarski, P; Aminophosphinic and Amino Phasphinic Acids, Chemistry and Biological Activity, 1st Edn 2000
19)Lever, A; Inorganic Electronic Spectroscopy, 2nd Edn 1984
20)Lukes, I; Dalton Trans 2007, 535
21)Maki, G; J Chem Phys 1958, 28, 651
22)Mikhailov, O; Trans Met Chem 2005, 30, 299
23)Nakamoto, K; Infrared Spectra of Inorganic and Coordination Compounds, 4th Edn 1996
24)Orvig, C; Inorg Chem 2002, 41, 685
25)Petering, H; Cancer Res 1964, 64, 367
26)Raman, N; J Chem Sci 2004, 116, 209
27)Scovill, J; J Med Chem 1982, 25, 1261
28)Sutton, D; Electronic Spectra of Transition Metal Complex, 1st Edn 1969
29)Tarafder, M; Polyhedron 2002, 21, 2683
30)Wildman, O; Chem Ber 1893, 26, 2613
31)Yousif, N; Syn React Inorg Met 2003, 33, 647
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

4. Synthesis of the new adducts of imines and enamines with PH acids and their derivatives
By: Prishchenko, Andrey A.; Livantsov, Mikhail V.; Novikova, Olga P.; Livantsova, Ludmila I.; Milaeva, Elena R.

Source: Heteroatom Chemistry, Volume: 20, Issue: 2, Pages: 70-80, Journal, 2009, CODEN: HETCE8, ISSN: 1042-7163, DOI:
10.1002/hc.20513

Company/Organization: Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow, Russia, 119991

Accession Number: 2009:452024, CAN 151:403365, CAPLUS


Publisher: John Wiley & Sons, Inc.
Language: English

Abstract
SciFinder Page 19
A nucleophilic or radical addn. of esters of trivalent organophosphorus acids with PH fragments to various imines and
enamines is proposed as convenient methods for the synthesis of substituted aminomethyl organophosphorus compds.
with three-coordinate, four-coordinate and five-coordinate phosphorus derivs. Example compds. thus prepd. included 4-
[1-(1,4,6,9-tetraoxa-55-phosphaspiro[4.4]non-5-yl)propyl]morpholine and 5,5'-[1,2-ethanediylbis(oxy)]bis[2,2,3,3-
tetramethyl-1,4,6,9-tetraoxa-55-phosphaspiro[4.4]nonane], [1-(4-morpholinyl)cyclohexyl]phosphonous acid
bis(trimethylsilyl) ester, etc. Also, functionalized derivs. of these compds. with acyl and methanesulfonyl moieties were
synthesized and some properties of the obtained compds. were described.
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Section cross-reference(s):27, 28
Concepts
Imines
aldimines; prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or
enamines with organophosphorus acids
Reactant; Reactant or reagent
Group 15 element compounds
hypophosphites; prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of
imines or enamines with organophosphorus acids
Reactant; Reactant or reagent
Elimination reaction
Homolytic addition reaction
Nucleophilic addition reaction
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
Acid chlorides
Enamines
Imines
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
Reactant; Reactant or reagent
Phosphonates
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
Reactant; Synthetic preparation; Preparation; Reactant or reagent
Addition reaction
regioselective; prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of
imines or enamines with organophosphorus acids
Sulfonyl halides
sulfonyl chlorides; prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of
imines or enamines with organophosphorus acids
Reactant; Reactant or reagent
Substances
75-77-4 Chlorotrimethylsilane, reactions
124-63-0 Methanesulfonyl chloride
622-29-7 N-(Phenylmethylene)methanamine
670-80-4 4-(1-Cyclohexen-1-yl)morpholine
762-04-9 Diethyl phosphite
3646-10-4 1,4,6,9-Tetraoxa-55-phosphaspiro[4.4]nonane
4023-34-1 Cyclopropanecarbonyl chloride
6852-58-0 2-Methyl-N-(phenylmethylene)-2-propanamine
7182-09-4 1-(1-Propenyl)piperidine
7313-26-0 2,6-Bis(1,1-dimethylethyl)-4-[(phenylimino)methyl]phenol
7803-65-8 Ammonium hypophosphite
13114-23-3 N-[(4-Methoxyphenyl)methylene]methanamine
SciFinder Page 20
15430-99-6 1-(Diethylamino)-1-butene
15431-03-5 4-(1-Butenyl)morpholine
16273-54-4 N-(3-Pyridinylmethylene)methanamine
17599-61-0 1,1,1-Trimethyl-N-(phenylmethylene)silanamine
18389-64-5
20521-59-9 4-(1-Propen-1-yl)morpholine
21064-27-7 N-(Phenylmethylene)-2-propen-1-amine
30148-50-6 Phosphonous acid bis(trimethylsilyl ester)
30653-71-5 Dibutoxyphosphine
39558-97-9 N-(2-Furanylmethylene)methanamine
104971-42-8 Phosphonous acid ethyl trimethylsilyl ester
104971-44-0 Phosphonous acid butyl trimethylsilyl ester

prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids

Reactant; Reactant or reagent


51909-56-9P
64244-30-0P
64661-94-5P
131149-04-7P
345254-23-1P
476306-09-9P
524020-03-9P
524020-04-0P
1135948-75-2P
1135948-76-3P

prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
SciFinder Page 21

Reactant; Synthetic preparation; Preparation; Reactant or reagent

78-67-1 AIBN

prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids

Reagent; Reactant or reagent


61890-81-1P
61890-83-3P
63207-56-7P
87363-87-9P
93593-93-2P [(Methylamino)phenylmethyl]phosphonous acid bis(trimethylsilyl) ester
93594-00-4P [(Methylamino)phenylmethyl]phosphonous acid dibutyl ester
111603-66-8P
126129-14-4P [[(1,1-Dimethylethyl)amino]phenylmethyl]phosphonous acid
bis(trimethylsilyl) ester
146500-38-1P
146500-39-2P
146500-40-5P
146500-41-6P [1-(4-Morpholinyl)cyclohexyl]phosphonous acid bis(trimethylsilyl)
ester
148627-42-3P
148627-43-4P
148627-44-5P
159852-05-8P
215925-03-4P
215925-04-5P
215925-06-7P
215925-07-8P
215925-08-9P
420830-18-8P
420830-34-8P
423147-43-7P
524020-05-1P
909722-70-9P
1135948-77-4P
1135948-78-5P
1135948-79-6P
1135948-80-9P
1135948-81-0P
1135948-82-1P
1189114-82-6P
1189114-84-8P
1263215-98-0P
SciFinder Page 22
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids

Synthetic preparation; Preparation


Supplementary Terms
imine enamine radical nucleophilic addn phosphorus acid
Citations
1)Antonova, N; Dokl Akad Nauk (in Russian) 2008, 419, 342
2)Burgada, R; Tetrahedron 1971, 27, 5833
3)Hickmott, P; Tetrahedron 1982, 38, 1975
4)Hilgetag, G; Weygand- Hilgetag. Organisch-Chemische Experimentierkunst (in Russian) 1968
5)Katritzky, A; Synth Commun 1995, 25, 1187
6)Kolodiazhnyi, O; Usp Khim (in Russian) 2006, 75, 254
7)Kukhar, V; Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity 2000
8)Kukhar, V; Usp Khim (in Russian) 1987, 56, 1504
9)Laurenco, C; Tetrahedron 1976, 32, 2253
10)Livantsov, M; Zh Obsh Khim (in Russian) 1985, 55, 2226
11)Lutsenko, I; Zh Obsh Khim (in Russian) 1978, 48, 765
12)Malavand, C; Tetrahedron Lett 1975, 16, 3077
13)Nonhebel, D; Radicals 1979
14)Onysko, P; Zh Obsh Khim (in Russian) 1985, 55, 454
15)Optitz, G; Lieb Ann 1963, 665, 91
16)Petrov, K; Usp Khim (in Russian) 1974, 43, 2045
17)Prishchenko, A; Heteroatom Chem 2008, 19, 490
18)Romanov, G; Zh Obsh Khim (in Russian) 1984, 54, 1749
19)Tyurin, V; Russ Chem Bull 2007, 744
20)Uziel, J; Zh Org Khim (in Russian) 1997, 33, 1605
21)Wannagat, U; Chemische Berichte 1961, 94, 1540
22)Yamagishi, T; Tetrahedron 1999, 55, 12125
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

5. Synthesis and structural studies of new Mannich base ligands and their metal complexes
By: Al-Jeboori, Mohamad Jaber; Abdul-Ghani, Ahlam Jamil; Al-Karawi, Ahmed Jasim

Source: Transition Metal Chemistry (Dordrecht, Netherlands), Volume: 33, Issue: 7, Pages: 925-930, Journal, 2008, CODEN:
TMCHDN, ISSN: 0340-4285, DOI: 10.1007/s11243-008-9134-3

Company/Organization: Department of Chemistry, College of Education Ibn Al-Haitham, University of Baghdad, Baghdad, Iraq

Accession Number: 2008:1056318, CAN 151:258998, CAPLUS


Publisher: Springer
Language: English

Abstract
SciFinder Page 23
L1
The new Mannich bases bis(1,4-diphenylthiosemicarbazide methyl) phosphinic acid H3 and bis(1,4-
diphenylsemicarbazide methyl) phosphinic acid H3L2 were synthesized from the condensation of phosphinic acid,
formaldehyde with 1,4-diphenylthiosemicarbazide and 1,4-diphenylsemicarbazide, resp. Monomeric complexes of these
ligands, of general formulas K2[CrIII(Ln)Cl2], K3[MnII(Ln)Cl2] and K[M(Ln)] (M = Co(II), Ni(II), Cu(II), Zn(II) or Hg(II); n = 1,
2), are reported. The mode of bonding and overall geometry of the complexes were detd. through physicochem. and
spectroscopic methods. These studies revealed octahedral geometries for the Cr(III), Mn(II) complexes, square planar
for Co(II), Ni(II) and Cu(II) complexes and tetrahedral for the Zn(II) and Hg(II) complexes.
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
Mannich bases
metal complexes; prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and
diphenyl(thio)semicarbazide and their metal complexes
Synthetic preparation; Preparation
Transition metal complexes
prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and diphenyl(thio)semicarbazide and
their metal complexes
Synthetic preparation; Preparation
Substances
621-12-5 1,4-Diphenylsemicarbazide
1768-59-8 1,4-Diphenylthiosemicarbazide
6303-21-5 Phosphinic acid

prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and diphenyl(thio)semicarbazide and
their metal complexes

Reactant; Reactant or reagent


1177451-03-4P
1177451-05-6P

prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and diphenyl(thio)semicarbazide and
their metal complexes

Reactant; Synthetic preparation; Preparation; Reactant or reagent


1177451-06-7P
SciFinder Page 24

1177451-07-8P
SciFinder Page 25

1177451-10-3P
SciFinder Page 26

1177451-11-4P
SciFinder Page 27

1177451-12-5P
SciFinder Page 28

1177451-14-7P
SciFinder Page 29

1177451-15-8P
SciFinder Page 30

1177451-16-9P
SciFinder Page 31

1177451-17-0P
SciFinder Page 32

1177451-18-1P
SciFinder Page 33

1177451-19-2P
SciFinder Page 34

1177451-20-5P
SciFinder Page 35

1177451-21-6P
SciFinder Page 36

1177451-22-7P
SciFinder Page 37

prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and diphenyl(thio)semicarbazide and
their metal complexes

Synthetic preparation; Preparation


Supplementary Terms
prepn phosphinic acid diphenylsemicarbazide formaldehyde Mannich base metal complex
Citations
1)Abram, M; Z Anorg Allg Chem, doi:10.1002/1521-3749(200206)628:6<1419::AID-ZAAC1419>3.0 CO;2-M 2002, 628,
1419
2)Abu-Hussen, A; J Coord Chem, doi:10.1080/00958970412331272412 2004, 57, 973
3)Baghiaf, A; Polyhedron, doi:10.1016/S0277-5387(00)87036-9 1985, 4, 853
4)Birodar, N; Inorg Chem Acta, doi:10.1016/S0020-1693(00)81975-1 1976, 17, 157
5)Buchardt, J; Chem Eur J, doi:10.1002/(SICI)1521-3765(19991001)5:10<2877::AID-CHEM2877>3.0 CO;2-Z 1999, 5,
2877
6)Chen, H; J Med Chem 2000, 43, 1348
7)Chkaku, N; Inorg Chem 1971, 10, 768
8)Deshmuck, M; Orent J Chem 1995, 11, 185
9)El-Asmy, A; Int J Pure Appl Chem 2006, 1, 75
10)El-Asmy, A; J Coord Chem 2005, 58, 1735
11)El-Said, F; Transit Met Chem 2003, 28, 954
12)El-Shazly, R; Spectro Chim Acta, doi:10.1016/j saa 2004.02.035 2005, 61, 243
13)Figgis, B; Introduction to ligand field 1966
SciFinder Page 38
14)Geary, W; Coord Chem Rev, doi:10.1016/S0010-8545(00)80009-0 1971, 7, 81
15)Haidue, L; Coord Chem Rev, doi:10.1016/0010-8545(90)80065-2 1990, 99, 253
16)Kafarski, P; Aminophosphinic and amino phosphinic acids, chemistry and biological activity, 1st edn 2000
17)Klayman, D; J Med Chem 1979, 22, 855
18)Lever, A; Inorganic electronic spectroscopy, 2nd edn 1984
19)Lukes, I; Dalton Trans 2007, 535
20)Maki, G; J Chem Phys, doi:10.1063/1.1744207 1958, 28, 651
21)Mishra, A; J Indian Counc Chem 1994, 10, 2
22)Nakamoto, K; Infrared spectra of inorganic and coordination compounds, 4th edn 1996
23)Orvig, C; Inorg Chem, doi:10.1021/ic0014179 2001, 40, 3734
24)Orvig, C; Inorg Chem, doi:10.1021/ic010716a 2002, 41, 685
25)Pogni, R; J Inorg Biochem, doi:10.1016/S0162-0134(99)00166-X 2000, 79, 333
26)Raman, N; J Chem Sci 2004, 116, 209
27)Rerrari, M; J Inorg Biochem, doi:10.1016/S0162-0134(02)00428-2 2002, 90, 113
28)Sutton, D; Electronic spectra of transition metal complex, 1st edn 1969
29)Tarafder, M; Polyhedron 2002, 21, 2683
30)Yousif, N; Synthesis and reactivity in inorganic and metal-organic chemistry 2003, 33, 647
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

6. Acylation of aryl-substituted bis(aminomethyl)phosphinic acids


By: Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; Milaeva, E. R.

Source: Russian Journal of General Chemistry, Volume: 78, Issue: 2, Pages: 324-326, Journal, 2008, CODEN: RJGCEK, ISSN: 1070-
3632, DOI: 10.1134/S1070363208020278

Company/Organization: Lomonosov Moscow State University, Moscow, Russia, 119992

Accession Number: 2008:452245, CAN 150:374613, CAPLUS


Publisher: Pleiades Publishing, Ltd.
Language: English

Abstract
The title reaction is described. Thus, acylation of HOP(O)P[CH(NHMe)Ph]2 with Ac2O or oleoyl chloride gave isomers of
HOP(O)[CH(NMeAc)Ph]2 and HOP(O)[CH(NMeCOR)Ph]2 (R = oleyl) resp.
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Concepts
Acylation
acylation of aryl-substituted bis(aminomethyl)phosphinic acids
Substances
112-77-6 Oleoyl chloride
345254-23-1
1135948-75-2

acylation of aryl-substituted bis(aminomethyl)phosphinic acids

Reactant; Reactant or reagent


1135948-76-3P
SciFinder Page 39

acylation of aryl-substituted bis(aminomethyl)phosphinic acids

Reactant; Synthetic preparation; Preparation; Reactant or reagent


1135948-77-4P
1135948-78-5P
1135948-79-6P
1135948-80-9P
1135948-81-0P
1135948-82-1P

acylation of aryl-substituted bis(aminomethyl)phosphinic acids

Synthetic preparation; Preparation


Supplementary Terms
acylation aryl aminomethyl phosphinic acid
Citations
1)Kolodyazhnyi, O; Usp Khim 2006, 75, 254
2)Kukhar, V; Usp Khim 1987, 56, 1504
3)Petrov, K; Usp Khim 1974, 43, 2045
4)Prishchenko, A; Zh Obshch Khim 1997, 67, 1914
5)Prishchenko, A; Zh Obshch Khim 1998, 68, 514
6)Prishchenko, A; Zh Obshch Khim 2007, 77, 1574
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

7. Complexation properties of the di-, tri-, and tetraacetate derivatives of bis(aminomethyl)phosphinic acid
By: Tircso, Gyula; Benyei, Attila; Kiraly, Robert; Lazar, Istvan; Pal, Robert; Brucher, Erno
SciFinder Page 40
Source: European Journal of Inorganic Chemistry, Issue: 5, Pages: 701-713, Journal, 2007, CODEN: EJICFO, ISSN: 1434-1948, DOI:
10.1002/ejic.200600891

Company/Organization: Department of Inorganic and Analytical Chemistry, University of Debrecen, Debrecen, Hung., 4010

Accession Number: 2007:238401, CAN 147:365554, CAPLUS


Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Language: English

Abstract
N-Carboxymethyl-substituted bis(aminomethyl)phosphinic acids R1R2NCH2P(O)(OH)CH2NR3R4 (HL0, R1-R4 = H; H3L1,
R1 = R3 = H, R2 = R4 = CH2CO2H; H3L2, R1 = R2 = H, R3 = R4 = CH2CO2H; H4L3, R1 = H, R2 = R3 = R4 = CH2CO2H;
H5L4, R1-R4 = CH2CO2H) were prepd. by condensation of amines, (dibenzylamine, iminodiacetic acid, N-benzylglycine)
with formaldehyde and H3PO2 with subsequent benzylic deprotection and carboxyalkylation by Br2CH2CO2H. The
ligands L0-L4 can be considered as di- (L1, L2), tri- (L3) and tetraacetate (L4) derivs. of bis(aminomethyl)phosphinic acid
(L0); their complexation equil. involving Mg2+, Ca2+, Ni2+, Cu2+, Zn2+, Cd2+, and Pb2+ were studied by pH potentiometry.
The first two protonation consts. of the ligands are lower than those of the analogous diaminopolycarboxylates due to the
electron-withdrawing effect of the phosphinate group. The asym. ligands L2 and L3 and their complexes are protonated
first at the primary (NH2) and secondary (NH) amine groups, resp. The ligands L0, L1, L2, and L3 form the species ML,
MLH, ML2, and ML2H whereas heptadentate L4 forms very stable ML complexes, protonated (MLH and MLH2) species
and, unlike the other ligands, it also forms dinuclear M2L complexes. The stability consts. of the complexes of L0, L1, L2,
and L3 are generally lower, while those of the L4 are similar or higher, than those of the analogous diaminocarboxylate
derivs. The phosphinate group is not directly coordinated to the metal ions but may contribute to the stability by
increasing the electrostatic interaction, which is significant for the complexes of L4. The 1H NMR spectra of complexes
ZnL2, ZnL3, and ZnL4 show an AB multiplet pattern for the protons of the iminodiacetate moiety of the ligands, which
indicates the long half-life of the Zn2+-N bond and the rigid structure of this segment of the complexes. The solid-state
structure of the ligand [H5L3]Cl and complex K[CuL1]H2O have been detd. by x-ray diffraction techniques. The
arrangement of the ligand L1 is square planar around Cu2+ with two nitrogen and carboxylate oxygen donor atoms,
although the axial proximity of a carboxylate and a phosphinate oxygen atom in two neighboring mols. results in a
distorted octahedral coordination.
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Section cross-reference(s):75, 78, 79
Concepts
Amines
aminophosphinates, acetate derivs.; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs. and formation
consts. of metal complexes with acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
Diamines
Phosphinates
aminophosphinates, acetate derivs.; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and
formation consts. of metal complexes with acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
Carboxylic acids
complexes, aminophosphinates, acetate derivs.; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs.,
acidity and formation consts. of metal complexes with acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
Protonation
const.; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal
complexes with acetate-phosphinate diamine chelate complexons
Crystal structure
Molecular structure
of copper complex with phosphinate-diacetate diamine chelate ligand
Acidity
Carboxyalkylation
Complexation
Condensation reaction
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs. and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
SciFinder Page 41
Chelating agents
Formation constant
Mannich reaction
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
Chelates
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
Complexing agents
transition metal complexes; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation
consts. of metal complexes with acetate-phosphinate diamine chelate complexons
Substances
949573-13-1P
949573-14-2P

crystal structure; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of
metal complexes with acetate-phosphinate diamine chelate complexons

Properties; Synthetic preparation; Preparation


949573-10-8P

mol. structure; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal
complexes with acetate-phosphinate diamine chelate complexons

Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
69219-70-1

prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons

Physical, engineering or chemical process; Properties; Reactant; Process; Reactant or reagent


949573-12-0P

prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons

Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent

14127-61-8 Calcium(2+), reactions


14280-50-3 Lead(2+), reactions
14701-22-5 Nickel(2+), reactions
15158-11-9 Copper(2+), reactions
22537-22-0 Magnesium(2+), reactions
22537-48-0 Cadmium(2+), reactions
23713-49-7 Zinc(2+), reactions

prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons

Physical, engineering or chemical process; Reactant; Process; Reactant or reagent


SciFinder Page 42
68358-05-4P
949573-08-4P

prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons

Physical, engineering or chemical process; Reactant; Synthetic preparation; Preparation; Process; Reactant or reagent

79-08-3 Bromoacetic acid


103-49-1 Dibenzylamine
142-73-4 Iminodiacetic acid
6303-21-5 Hypophosphorous acid
7689-50-1 N-Benzylglycine hydrochloride

prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons

Reactant; Reactant or reagent


21852-07-3P

68733-66-4P
69219-71-2P
949573-07-3P
949573-09-5P
949573-11-9P

prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons

Reactant; Synthetic preparation; Preparation; Reactant or reagent


Supplementary Terms
phosphinic acid aminomethyl acetate prepn metal complex formation const; protonation const phosphinic acid
aminomethyl acetate; Mannich condensation amine formaldehyde hypophosphorous acid prepn phosphinate acetate;
complexon phosphinate acetate diamine prepn aminomethyl phosphinic acid carboxyalkylation; crystal structure copper
phosphinate acetate diamine chelate complex; mol structure copper phosphinate diacetate diamine chelate complex
Citations
1)Aime, S; Tetrahedron Lett 2002, 43, 8387
2)Allen, F; Acta Crystallogr, Sect B 2002, 58, 380
3)Altomare, A; J Appl Crystallogr 1993, 26, 343
4)Baes, C; The Hydrolysis of Cations 1976, 512
5)Bates, G; J Chem Soc, Dalton Trans 1996, 2693
SciFinder Page 43
6)Bazakas, K; J Chem Soc, Dalton Trans 1995, 1133
7)Broan, C; J Chem Soc, Chem Commun 1990, 1739
8)Collinsova, M; Curr Med Chem 2000, 7, 629
9)Day, R; Anal Chem 1964, 36, 1073
10)Dhansay, M; J Coord Chem 1993, 28, 133
11)Dhansay, M; J Phys Org Chem 1990, 3, 248
12)Farrugia, L; WINGX-97 system 1996
13)Hancock, R; Inorg Chem 1990, 29, 1968
14)Hermann, P; J Chem Soc, Dalton Trans 1995, 2605
15)Hermann, P; J Chem Soc, Dalton Trans 1995, 2611
16)Irving, H; Anal Chim Acta 1967, 38, 475
17)Jaszberenyi, Z; Dalton Trans 2005, 2713
18)Kiss, T; J Chem Soc, Dalton Trans 1990, 377
19)Kiss, T; J Chem Soc, Dalton Trans 1991, 2275
20)Kubicek, V; Dalton Trans 2003, 3927
21)Kukhar, V; Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity 2000, 660
22)Lazar, I; Inorg Chem 1991, 30, 5016
23)Liu, S; Jiegou Huaxue (Chinese J Struct Chem) 1999, 18, 38
24)Lukas, M; J Chem Soc, Dalton Trans 2001, 2850
25)Lukes, I; J Chem Soc, Dalton Trans 1992, 939
26)Maier, L; Helv Chim Acta 1967, 50, 1742
27)Maier, L; J Organomet Chem 1979, 178, 157
28)Maier, L; Phosphorus Sulfur Silicon Relat Elem 1980, 8, 67
29)Martell, A; Critical Stability Constants 1974, 1-6
30)Matovic, Z; Inorg Chim Acta 1998, 268, 221
31)Nagy, N; J Inorg Biochem 2004, 98, 1655
32)Natchev, A; Liebigs Ann Chem 1988, 861
33)Parker, D; J Chem Soc, Chem Commun 1992, 1441
34)Peyman, A; Tetrahedron Lett 1992, 33, 4549
35)Pulukkody, K; J Chem Soc, Perkin Trans 2 1993, 605
36)Rohovec, J; Eur J Inorg Chem 2000, 195
37)Rohovec, J; J Chem Soc, Dalton Trans 1996, 2685
38)Rohovec, J; J Chem Soc, Dalton Trans 2000, 141
39)Sheldrick, G; SHELX-97, A Program for Crystal Structure Refinement 1997
40)Song, B; Inorg Chem 2002, 41, 685
41)Thomas, W; Prog Nucl Magn Reson Spectrosc 1997, 30, 183
42)Van Geet, A; Anal Chem 1970, 42, 679
43)Varga, T; ACH -- Models in Chemistry 1999, 136, 431
44)Varga, T; Synth Commun 1997, 27, 2899
45)Villanueva, N; Inorg Chem 1998, 37, 685
46)Xu, L; Inorg Chem 2001, 40, 3734
47)Zekany, L; Computational Methods for Determination of Formation Constants 1985, 291
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.


SciFinder Page 44
8. Preparation of new bis(aminomethyl)phosphinic acid derivatives
By: Peyman, Anuschirwan; Spanig, Joerg; Budt, Karl-Heinz
Assignee: Hoechst A.-G., Germany

Patent Information: Oct 06, 1994, DE 4310815, A1

Application: Apr 02, 1993, DE 1993-4310815

Priority: Apr 02, 1993, DE 1993-4310815, Mar 24, 1994, WO 1994-EP950

Source: Ger. Offen., 14 pp., Patent, 1994, CODEN: GWXXBX

Classifications: Main IPC: C07F009-32, Secondary IPC: C07F009-38; C07F009-40;

Accession Number: 1995:234775, CAN 122:10259, CAPLUS


Language: German

Abstract
The prepn. of new title compds., R4NHCHR2P(O)(OR5)CHR3NHR4 [R2, R3 = H, (un)substituted C1-18 alkyl, C2-18 alkenyl,
C2-18 alkynyl, etc.; R4 = protecting group for amino group; R5 = C1-18 alkyl, C2-18 alkenyl, C2-18 alkynyl, C6-12 aryl, C7-20
arylalkyl, etc.], useful in pharmaceutical as well as in agriculture chem., is described. Thus, reaction of Et bis(N-
benzoylamino(bromo)methyl)phosphonate (prepn. given) with 1-morpholino-1-cyclohexene in the presence of N-
ethyldiisopropylamine in THF gave 35% diastereoisomeric mixt. of title compd. Et bis(N-benzoylamino(2-
cyclohexanone)methyl)phosphonate.

Patent Information
Patent No. Kind Date Application No. Date
DE 4310815 A1 Oct 06, 1994 DE 1993-4310815 Apr 02, 1993
WO 9422879 A1 Oct 13, 1994 WO 1994-EP950 Mar 24, 1994
EP 691975 A1 Jan 17, 1996 EP 1994-912541 Mar 24, 1994
EP 691975 B1 Jun 04, 1997
JP 08508276 T Sep 03, 1996 JP 1994-521647 Mar 24, 1994
JP 3994171 B2 Oct 17, 2007
AT 154024 T Jun 15, 1997 AT 1994-912541 Mar 24, 1994
ES 2102852 T3 Aug 01, 1997 ES 1994-912541 Mar 24, 1994
US 5608098 A Mar 04, 1997 US 1995-525787 Sep 28, 1995

Priority Application
DE 1993-4310815 A Apr 02, 1993
WO 1994-EP950 W Mar 24, 1994

Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Substances
159532-09-9P
159532-10-2P
SciFinder Page 45
159532-11-3P
159532-12-4P
159532-13-5P
159532-14-6P
159532-15-7P

prepn. of

Synthetic preparation; Preparation

98-88-4 Benzoyl chloride


122-52-1 Triethyl phosphite
670-80-4 1-Morpholino-1-cyclohexene
6921-34-2 Benzylmagnesium chloride
24424-99-5
68358-05-4

prepn. of new bis(aminomethyl)phosphinic acid derivs.

Reactant; Reactant or reagent


127590-11-8P

152862-45-8P
152862-46-9P
155387-28-3P
159532-03-3P
159532-04-4P
159532-05-5P
159532-06-6P
159532-07-7P
159532-08-8P

prepn. of new bis(aminomethyl)phosphinic acid derivs.

Reactant; Synthetic preparation; Preparation; Reactant or reagent


Supplementary Terms
aminomethyl phosphonate; phosphinic acid deriv aminomethyl
Tags
0 Tags
Comments
0 Comments
SciFinder Page 46

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

9. Preparation of amino acid and peptidylphosphinates and related compounds as retroviral protease inhibitors
By: Budt, Karl Heinz; Peyman, Anuschirwan
Assignee: Hoechst A.-G., Germany

Patent Information: Jun 20, 1991, DE 4039569, A1

Application: Dec 11, 1990, DE 1990-4039569

Priority: Dec 16, 1989, DE 1989-3941607, Jun 13, 1990, DE 1990-4018942, Dec 14, 1990, US 1990-627818, Dec 16, 1993, US 1993-167613,
Aug 19, 1994, US 1994-293112

Source: Ger. Offen., 42 pp., Patent, 1991, CODEN: GWXXBX

Classifications: Main IPC: C07F009-30, Secondary IPC: C07K005-06; C07F009-32; C07F009-36; C07K005-04; A61K031-66; A61K037-02;

Accession Number: 1991:656657, CAN 115:256657, CAPLUS


Language: German

Abstract
AR4NCR2R3QCRR1NR6A1 [Q = S, SO, SO2, R9(R5Y)P, R9(R7R8N)P; A,A1 = DEnFoGp; E, F, G = (un)natural amino acid,
azaaminoacid-, or imino acid residue, n, o, p = 0, 1; D = H, carboxy, SH, OH, alkoxy, amino, amidino, carbamoyl,
alkanoyloxy, F, Cl, Br, iodo, (substituted) aminomethylcarbonyl, propionyl, etc.; Y = O, S; R,R2 = H, CO2H, SH, OH,
alkoxy, carbamoyl, alkanoyloxy, carboxy, alkoxycarbonyl, F, Cl, Br, iodo, amino, amidino, alkylsulfonyl, alkylsufinyl,
alkylthio, hydroxamino, sulfamoyl, CHO, etc.; R1,R3R4,R6 = H, alkyl; R2R4,RR6 = atoms to complete (unsatd.) (bicyclic) 5-
12 membered rings; R5 = H, alkyl, alkenyl, alkynyl, aralkyl, aryl, (substituted) cycloalkyl, cation, phosphate prodrug
moiety; R7,R8 = H, alkyl, alkenyl, alkynyl, aryl, (substituted) aralkyl; R7R8 = atoms to complete a ring contg. 2-6 C atoms;
R9 = O, S], were prepd. as retroviral protease inhibitors (no data). Thus, (H2NCH2)2P(O).HCl (prepn. starting H3PO2 and
H2CO given) and BOC-Val-OH (BOC = Me3CO2C) were coupled in DMF at 0 using N-ethylmorpholine,
hydroxybenzotriazole, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to give 81% (BOC-Val-
NHCH2)2P(O)(OH).

Patent Information
Patent No. Kind Date Application No. Date
DE 4039569 A1 Jun 20, 1991 DE 1990-4039569 Dec 11, 1990
EP 435059 A1 Jul 03, 1991 EP 1990-123779 Dec 11, 1990
EP 435059 B1 Nov 05, 1997
AT 159946 T Nov 15, 1997 AT 1990-123779 Dec 11, 1990
ES 2110404 T3 Feb 16, 1998 ES 1990-123779 Dec 11, 1990
FI 9006140 A Jun 17, 1991 FI 1990-6140 Dec 13, 1990
SciFinder Page 47
CA 2032303 A1 Jun 17, 1991 CA 1990-2032303 Dec 14, 1990
CA 2032303 C Mar 19, 2002
NO 9005410 A Jun 17, 1991 NO 1990-5410 Dec 14, 1990
AU 9068025 A Jun 20, 1991 AU 1990-68025 Dec 14, 1990
AU 641197 B2 Sep 16, 1993
ZA 9010068 A Sep 25, 1991 ZA 1990-10068 Dec 14, 1990
HU 59147 A2 Apr 28, 1992 HU 1990-8276 Dec 14, 1990
JP 05331067 A Dec 14, 1993 JP 1990-419203 Dec 14, 1990
JP 2816253 B2 Oct 27, 1998
KR 203231 B1 Jun 15, 1999 KR 1990-20696 Dec 15, 1990
US 5629431 A May 13, 1997 US 1995-479562 Jun 07, 1995

Priority Application
DE 1989-3941607 A1 Dec 16, 1989
DE 1990-4018942 A1 Jun 13, 1990
US 1990-627818 B1 Dec 14, 1990
US 1993-167613 B1 Dec 16, 1993
US 1994-293112 B1 Aug 19, 1994

Indexing
Amino Acids, Peptides, and Proteins (Section 34-3)
Section cross-reference(s):1
Concepts
Peptides, preparation
phosphinate derivs., prepn. of, as retroviral protease inhibitors
Synthetic preparation; Preparation
Amino acids, preparation
phosphinates, prepn. of, as retroviral protease inhibitors
Synthetic preparation; Preparation
Immunodeficiency
acquired immune deficiency syndrome, deriv. of, amino acid- and peptidylphosphinates for
Substances
13734-41-3

condensation and coupling of, with aminomethylphosphinate, in prepn. of retroviral protease inhibitor

Reactant; Reactant or reagent


1149-26-4

condensation of, with aminomethylphosphinate, in prepn. of retroviral protease inhibitor

Reactant; Reactant or reagent

5824-40-8 Triphenylmethylamine

condensation of, with phenylacetaldehyde

Reactant; Reactant or reagent


103-49-1

condensation of, with phosphinic acid


SciFinder Page 48
Reactant; Reactant or reagent

122-78-1 Phenylacetaldehyde

condensation of, with triphenylmethylamine

Reactant; Reactant or reagent


13734-34-4
137331-84-1

coupling of, with aminomethylphosphinate, in prepn. of retroviral protease inhibitor

Reactant; Reactant or reagent


137283-67-1

in prepn. of peptidylphosphinate retroviral protease inhibitor

Reactant; Reactant or reagent


4530-20-5

peptide coupling of, in prepn. of peptidylphosphinate retroviral protease inhibitor

Reactant; Reactant or reagent


2488-15-5
5241-64-5
13139-16-7
13726-67-5
18942-49-9

peptide coupling of, in prepn. of retroviral protease inhibitor

Reactant; Reactant or reagent

2074-67-1P Bis(hydroxymethyl)phosphinic acid


13274-83-4P Bis(chloromethyl)phosphinic acid
13482-64-9P
68358-03-2P

127590-10-7P

prepn. of, as intermediate for peptidylphosphinate retroviral protease inhibitor

Synthetic preparation; Preparation


137283-68-2P
137283-69-3P
137283-70-6P
SciFinder Page 49
137283-71-7P
137283-72-8P
137283-73-9P
137283-74-0P
137283-75-1P
137283-76-2P
137283-77-3P
137283-78-4P
137283-79-5P
137283-80-8P
137283-81-9P
137283-82-0P
137283-83-1P
137283-84-2P
137283-85-3P
137283-86-4P
137283-87-5P
137283-88-6P
137283-89-7P
137283-90-0P

137283-91-1P
137283-92-2P
SciFinder Page 50
137283-93-3P
137283-94-4P
137283-95-5P
137283-96-6P
137306-09-3P
137331-82-9P
137331-83-0P

prepn. of, as retroviral protease inhibitor

Biological activity or effector, except adverse; Biological study, unclassified; Synthetic preparation; Biological study;
Preparation

6303-21-5 Phosphinic acid

reaction of, in prepn. of peptidylphosphinates

Reactant; Reactant or reagent

9001-92-7 Protease

retroviral, inhibitors, amino acid- and peptidylphosphinates

Reactant; Reactant or reagent


Supplementary Terms
phosphinate amino acid AIDS treatment; peptidylphosphinate prepn retroviral protease inhibitor; AIDS treatment
peptidylphosphinate
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

10. Preparation of bis(aminomethyl)phosphinic acid from acylaminomethanols and trivalent phosphorus halides
By: Kober, Reiner; Seele, Rainer; Steglich, Wolfgang; Schrader, Thomas
Assignee: BASF A.-G., Germany

Patent Information: Jan 25, 1990, DE 3824961, A1

Application: Jul 22, 1988, DE 1988-3824961

Priority: Jul 22, 1988, DE 1988-3824961

Source: Ger. Offen., 4 pp., Patent, 1990, CODEN: GWXXBX


Classifications: Main IPC: C07F009-30

Accession Number: 1990:406598, CAN 113:6598, CAPLUS


Language: German

Abstract
(H2NCH2)2P(O)(OH) (I), a known plant growth inhibitor (West German OS 2,805,074) was prepd. by condensation of
RCONHCH2OH [R = (substituted) alkyl, cycloalkyl, aralkyl, aryl] with a trivalent P halide optionally in the presence of an
alkali, alk. earth, or ammonium bromide or iodide to give (RCONHCH2)2P(O)(OH) (II), followed by hydrolysis. Thus, a
mixt. of PhCONHCH2OH (prepn. given) and PCl3 was heated to 150 over 30 min. H2O was added to the cooled mixt.
and the residue was refluxed 5 min in EtOAc to give 61% II (R = Ph). The latter was heated at 120 in concd. HCl for 16
h to give 94% I.
SciFinder Page 51

Patent Information
Patent No. Kind Date Application No. Date
DE 3824961 A1 Jan 25, 1990 DE 1988-3824961 Jul 22, 1988

Priority Application
DE 1988-3824961 Jul 22, 1988

Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Section cross-reference(s):5
Concepts
Plant hormones and regulators
bis(aminomethyl)phosphinic acid
Reactant; Reactant or reagent
Substances
7789-60-8 Phosphorus tribromide

condensation of, with hydroxymethylbenzamide

Reactant; Reactant or reagent

50-00-0 Formaldehyde, reactions

hydroxymethylation by, of benzamide

Reactant; Reactant or reagent

55-21-0 Benzamide

hydroxymethylation of

Reactant; Reactant or reagent

6282-02-6P N-Hydroxymethylbenzamide

prepn. and condensation of, with phosphorus tribromide

Synthetic preparation; Preparation

127590-11-8P Bis(N-benzoylaminomethyl)phosphinic acid


SciFinder Page 52
prepn. and hydrolysis of

Reactant; Synthetic preparation; Preparation; Reactant or reagent

127590-10-7P Bis(aminomethyl)phosphinic acid hydrochloride

prepn. of, from hydroxymethylbenzamide and phosphorus tribromide

Synthetic preparation; Preparation


Supplementary Terms
bisaminomethylphosphinate; phosphinate bisaminomethyl; acylaminomethanol phosphorus halide condensation;
aminomethylphosphinate
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

11. Zinc(2+)-catalyzed decomposition of a tris(imidazol-2-yl)phosphine. Crystal and molecular structure of


[bis(4,5-diisopropylimidazol-2-yl)phosphinic acid]dichlorozinc hydrate
By: Ball, R. G.; Brown, R. S.; Cocho, J. L.

Source: Inorganic Chemistry, Volume: 23, Issue: 15, Pages: 2315-18, Journal, 1984, CODEN: INOCAJ, ISSN: 0020-1669, DOI:
10.1021/ic00183a021

Company/Organization: Dep. Chem., Univ. Alberta, Edmonton, AB, Can., T6G 2G2

Accession Number: 1984:447613, CAN 101:47613, CAPLUS


Language: English

Abstract
The reaction of an EtOH soln. of bis(4,5-diisopropylimidazol-2-yl)(imidazol-2-yl)phosphine with aq. ZnCl2 results in the
formation of ZnCl2(OPR2OH)2.H2O (R = 4,5-diisopropylimidazol-2-yl), which was characterized by x-ray crystallog. The
complex crystallizes in the space group P21/c with a 9.805(3), b 26.202(7), c 10.924(3) , 111.79(2), and Z = 4. The
structure refined routinely to a final R of 6.6%. The structural results indicate that the original phosphine has undergone
oxidn. and replacement of an imidazole by OH-, the latter process apparently being promoted by the presence of ZnCl2.
Thus tris(imidazol-2-yl)phosphine-Zn2+ complexes, which are catalytically active models for the active site of carbonic
anhydrase, suffer an apparent Zn2+-promoted decompn., which accounts for the obsd. loss of activity when they are
allowed to stand in soln.
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Section cross-reference(s):7, 25, 29
Concepts
Crystal structure
Molecular structure
of [bis(diisopropylimidazolyl)phosphinic acid]dichlorozinc hydrate
Substances
7646-85-7 uses and miscellaneous

oxidn. and substitution of hydroxide for imidazole in bis(diisopropylimidazolyl)(imidazolyl)phosphine in presence of

Uses
89210-50-4

oxidn. and substitution of hydroxide for imidazole in, in presence of zinc chloride in aq. ethanol
SciFinder Page 53
Reactant; Reactant or reagent
90481-58-6P

prepn. and structure of

Properties; Synthetic preparation; Preparation


Supplementary Terms
imidazolylphosphine oxidn substitution zinc chloride; phosphine imidazolyl oxidn substitution zinc; structure zinc chloro
diisopropylimidazolylphosphinic acid
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

12. Organic phosphorus compounds. LXXI. Preparation, properties, and structure of


bis(aminomethyl)phosphinic acid, (H2NCH2)2P(O)OH
By: Maier, Ludwig

Source: Journal of Organometallic Chemistry, Volume: 178, Issue: 1, Pages: 157-69, Journal, 1979, CODEN: JORCAI, ISSN: 0022-
328X, DOI: 10.1016/S0022-328X(00)87867-5

Company/Organization: Agrochem. Div., Ciba-Geigy Ltd., Basel, Switz., CH-4002

Accession Number: 1980:6618, CAN 92:6618, CAPLUS


Language: English
SciFinder Page 54
Abstract
(H2NCH2)2P(O)OH.HCl, was prepd. by debenzylation of (PhCH2NHCH2)2P(O)OH.HCl with H using 5% Pd/C as catalyst,
and from (Me3CNHCH2)2P(O)OH, by isobutylene elimination in concd. aq. HBr at 175 in a sealed tube. Interaction of
(ClCH2)2P(O)OH with NH3 in an autoclave produced MeNHCH2P(O)(OH)2. Several derivs. of (H2NCH2)2P(O)OH such
as (RNHCH2)2P(O)OH (R = Bz, ClCH2CO), [H2NHNC(:NH)NHCH2]2P(O)OH and (Me3SiNHCH2)2P(O)OSiMe3 were
prepd.
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Substances
2074-67-1P

prepn. and chlorination of

Reactant; Synthetic preparation; Preparation; Reactant or reagent


21852-07-3P

prepn. and debenzylation of

Reactant; Synthetic preparation; Preparation; Reactant or reagent


13482-64-9P

prepn. and hydrolysis of

Reactant; Synthetic preparation; Preparation; Reactant or reagent


13274-83-4P

prepn. and reaction with benzylamine

Reactant; Synthetic preparation; Preparation; Reactant or reagent


68358-05-4P

prepn. and reactions of

Reactant; Synthetic preparation; Preparation; Reactant or reagent


68358-04-3P
68358-06-5P
68358-07-6P
68358-08-7P
68358-09-8P
SciFinder Page 55
72190-58-0P
72190-59-1P

72190-60-4P
72190-61-5P
72190-62-6P

prepn. of

Synthetic preparation; Preparation


999-97-3
35600-34-1

reaction of, with bis(aminomethyl)phosphinic acid

Reactant; Reactant or reagent


6303-21-5

reaction of, with paraformaldehyde

Reactant; Reactant or reagent


30525-89-4

reaction of, with phosphinic acid

Reactant; Reactant or reagent


Supplementary Terms
aminomethylphosphinic acid; phosphinic acid aminomethyl; silylaminomethylphosphinic acid
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

13. Bis(aminomethyl)phosphinic acids


SciFinder Page 56
By: Maier, Ludwig
Assignee: Ciba-Geigy A.-G., Switz.

Patent Information: Aug 17, 1978, DE 2805074, A1

Application: Feb 07, 1978, DE 1978-2805074

Priority: Feb 10, 1977, CH 1977-1614

Source: Ger. Offen., 20 pp., Patent, 1978, CODEN: GWXXBX

Accession Number: 1978:615549, CAN 89:215549, CAPLUS


Language: German

Abstract
H3PO2 and paraformaldehyde gave 86.2% (HOCH2)2P(O)OH, which, with SOCl2 gave 94.5% (ClCH2)2P(O)OH (I).
Amination of I with PhCH2NH2 gave 84.8% (PhCH2NHCH2)P(O)OH, debenzylation of which gave 87.4%
(H2NCH2)2P(O)OH, useful as a plant growth regulator.
Patent Information
Patent No. Kind Date Application No. Date
DE 2805074 A1 Aug 17, 1978 DE 1978-2805074 Feb 07, 1978
CH 627477 A5 Jan 15, 1982 CH 1977-1614 Feb 10, 1977
US 4171969 A Oct 23, 1979 US 1978-875842 Feb 07, 1978
FR 2380289 A1 Sep 08, 1978 FR 1978-3565 Feb 08, 1978
FR 2380289 B1 Dec 17, 1982
JP 53098929 A Aug 29, 1978 JP 1978-14018 Feb 09, 1978
GB 1594436 A Jul 30, 1981 GB 1978-5265 Feb 09, 1978

Priority Application
CH 1977-1614 A Feb 10, 1977

Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Section cross-reference(s):5
Concepts
Plant hormones and regulators
bis(aminomethyl)phosphinic acid
Reactant; Reactant or reagent
Substances
2074-67-1P

prepn. and chlorination of

Reactant; Synthetic preparation; Preparation; Reactant or reagent


68358-04-3P

prepn. and dealkylation of

Reactant; Synthetic preparation; Preparation; Reactant or reagent


68358-03-2P

prepn. and debenzylation of


SciFinder Page 57

Reactant; Synthetic preparation; Preparation; Reactant or reagent


21852-07-3P

68358-05-4P
68358-06-5P
68358-07-6P
68358-08-7P
68358-09-8P

prepn. of

Synthetic preparation; Preparation


13274-83-4

reaction with amines

Reactant; Reactant or reagent

75-64-9 reactions
100-46-9 reactions

reaction with bis(chloromethyl)phosphinic acid

Reactant; Reactant or reagent


Supplementary Terms
plant growth regulator aminomethylphosphinate; aminomethylphosphinic acid bis; phosphinic acid bisaminomethyl
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

14. Inorganic coordination polymers. XXII. Manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) bis[bis(N-
phenylaminomethyl)phosphinates]. Effects of coordinating side groups
By: Gillman, H. D.; Eichelberger, J. L.

Source: Inorganica Chimica Acta, Volume: 24, Issue: 1, Pages: 31-4, Journal, 1977, CODEN: ICHAA3, ISSN: 0020-1693, DOI:
10.1016/S0020-1693(00)93846-5

Company/Organization: Technol. Cent., Pennwalt Corp., King of Prussia, PA, USA


SciFinder Page 58
Accession Number: 1978:572760, CAN 89:172760, CAPLUS
Language: English

Abstract
The metal(II) bis[bis(N-phenylaminomethyl)phosphinates], M[OP(CH2NHPh)2O]2 (M = Mn, Co, Ni, Cu, and Zn), were
investigated. The Mn, Co, and Ni derivs. all have similar structures with octahedrally coordinated metal centers, the Cu
deriv. is probably tetragonally distorted octahedral and the Zn deriv. is tetrahedral. All of these compds. contain some
coordinating amine groups except the Zn complex in which no amine groups coordinate. Most likely, all of these
compds. contain sym. bridging O,O'-phosphinate groups. The thermal stabilities of these complexes are markedly
different from one another and appear to be dependent on the ligand-field stabilization energies but not on the chelation
of the amine groups.
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
Transition metals, compounds
with bis(phenylaminomethyl)phosphinate ligands
Reactant; Reactant or reagent
Substances
68010-31-1P

68026-30-2P

68026-29-9
C28 H32 Cu N4 O4 P2

68026-32-4P
SciFinder Page 59

68026-31-3
C28 H32 N4 Ni O4 P2

68026-34-6P

68026-33-5
C28 H32 Co N4 O4 P2

68026-36-8P

68026-35-7
C28 H32 Mn N4 O4 P2

prepn. of

Synthetic preparation; Preparation


Supplementary Terms
transition metal phenylaminomethyl phosphinate; manganese phenylaminomethyl phosphinate complex; cobalt
phenylaminomethyl phosphinate complex; nickel phenylaminomethyl phosphinate complex; copper phenylaminomethyl
phosphinate complex; zinc phenylaminomethyl phosphinate complex
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

15. Inorganic coordination polymers. XXI. Manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) bis(N-
phenylaminomethyl) phosphinates. Effects of coordinating side groups
By: Eichelberger, J. L.; Gillman, H. D.

Source: U. S. NTIS, AD Rep., Issue: AD-A035099, 18 pp., Report, 1977, CODEN: XADRCH
SciFinder Page 60
Company/Organization: Res. Dev. Dep., Pennwalt Corp., King of Prussia, PA, USA

Accession Number: 1977:415290, CAN 87:15290, CAPLUS

Publisher: From Gov. Rep. Announce. Index (U. S.) 1977, 77(8), 119, Avail. NTIS
Language: English

Abstract
The metal(II) bis[bis(phenylaminomethyl)phosphinates], M[O2P(CH2NHPh)2]2 (M = Mn, Co, Ni, Cu, and Zn) were
investigated. The Mn, Co, and Ni derivs. all have similar structures with octahedrally coordinated metal centers, the Cu
deriv. is probably tetragonally distorted octahedral, and the Zn deriv. is tetrahedral. All of these compds. contain some
coordinating amine groups except the Zn complex in which no amine groups coordinate. Most likely, all of these
compds. contain sym. bridging O,O'-phosphinate groups. The thermal stabilities of these complexes are markedly
different from one another and appear to be dependent on the ligand-field stabilization energies but not on the chelation
of the amine groups.
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
Energy level splitting
crystal-field, of transition metal bis(phenylaminomethyl)phosphinate-bridged complexes, thermal stability in relation to
Substances
7439-96-5DP bis(phenylaminomethyl)phosphinate polymeric complexes
7440-02-0DP bis(phenylaminomethyl)phosphinate polymeric complexes
7440-48-4DP bis(phenylaminomethyl)phosphinate polymeric complexes
7440-50-8DP bis(phenylaminomethyl)phosphinate polymeric complexes
7440-66-6DP bis(phenylaminomethyl)phosphinate polymeric complexes
20384-96-7DP transition metal polymeric complexes

prepn. of

Synthetic preparation; Preparation


Supplementary Terms
transition metal phosphinate bridged complex; aminomethyl phosphinate bridged metal complex; zinc aminomethyl
phosphinate bridged polymer; manganese aminomethyl phosphinate bridged polymer; cobalt aminomethyl phosphinate
bridged polymer; nickel aminomethyl phosphinate bridged polymer; copper aminomethyl phosphinate bridged polymer
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

16. Synthesis and properties of bin(N-alkyl(aryl)aminomethyl)phosphinic acids


By: Il'ina, M. K.; Shermergorn, I. M.
SciFinder Page 61
Source: Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, Issue: 8, Pages: 1860-2, Journal, 1968, CODEN: IASKA6, ISSN:
0002-3353

Company/Organization: Inst. Org. Fiz. Khim. im. Arbuzova, Kazan, USSR

Accession Number: 1969:37885, CAN 70:37885, CAPLUS


Language: Russian

Abstract
Heating 284 g. PhNH2 and 50 g. (ClCH2)2PO2H 10 hrs. at 110-20 gave 63% (PhNHCH2)2PO2H (I) m. 180-1;
benzylamine similarly gave 72% (PhCH2NHCH2)2PO2HHCl, m. 220-2, while allylamine gave 33%
(CH2:CHCH2NHCH2)2PO2HHCl m. 200-2, and BuNH2 gave (BuNHCH2)2PO2HHCl, m. 240-2; propylamine gave
47% (PhNHCH2)2PO2HHCl, m. 238-9. I and CH2:CMeCOCl in CHCl3 in the presence of aq. NaOH gave in 1 hr. at 0,
followed by acidification with concd. HCl, and evapn. of org. layer and treatment with Et2O a ppt. of
[[PhN(COCMe:CH2)CH2]2PO2H]2CH2:CMeCO2Na, m. 239-41. Acidification with HCl gave [PhN(COCMe:CH2)CH2]2-
PO2HHCl m. 70-1;similarly obtained was [PhCH2N(COCMe:-CH2)CH2]2PO2H, m. 146-7, via
[PhCH2N(COCMe:CH2)CH2]2PO2Na, m. 272.5-3.5.
Indexing
Organometallic and Organometalloidal Compounds (Section 29)
Substances
1071708-06-9P

1087409-20-8P

Synthesis and properties of bin(N-alkyl(aryl)aminomethyl)phosphinic acids

Synthetic preparation; Properties; Preparation


20384-96-7P

21852-07-3P
SciFinder Page 62

21852-08-4P
21852-09-5P
21852-10-8P

21852-11-9P
21852-12-0P
21852-13-1P
23273-72-5P

prepn. of

Synthetic preparation; Preparation


Supplementary Terms
phosphinic acid aminomethyl
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

17. Bis(N-alkyl- or arylaminomethyl)phosphonic acids


By: Il'ina, M. K.; Shermergorn, I. M.
Assignee: Arbuzov, A. E., Institute of Organic and Physical Chemistry

Patent Information: Mar 20, 1968, SU 213858

Application: Feb 06, 1967, SU

Source: U.S.S.R., Patent, 1968, CODEN: URXXAF

Accession Number: 1968:477476, CAN 69:77476, CAPLUS


Language: Russian
SciFinder Page 63
Abstract
The title acids are prepd. from the reaction of bis(chloromethyl)phosphinic acids with primary amines while heating to
110-120 in the corresponding amine.
Patent Information
Patent No. Kind Date Application No. Date
SU 213858 Mar 20, 1968 SU Feb 06, 1967

Indexing
Organometallic and Organometalloidal Compounds (Section 29)
Substances
20384-96-7P

20384-97-8P

prepn. of

Synthetic preparation; Preparation


Supplementary Terms
phosphonic acid
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

18. Sydonones. III. Reactions of lithium phenylsydone with acid nonmetallic chlorides
By: Suciu, Nausicaa; Mihai, Gheorghe

Source: Tetrahedron, Volume: 24, Issue: 1, Pages: 37-42, Journal, 1968, CODEN: TETRAB, ISSN: 0040-4020, DOI: 10.1016/0040-
4020(68)89005-2

Company/Organization: Centre Radiobiol. Mol. Biol., Bucharest, Rom.

Accession Number: 1968:29635, CAN 68:29635, CAPLUS


Language: English

Abstract
The reactions of lithium phenylsydnone (I) with the acid chloride of 3-phenylsydnonyl-4-carboxylic acid gave Q2CO (Q =
phenylsydnonyl) and Q2C(OH)H. I with acetyl, valerianyl, and benzoyl gave Q2C(OH)R (R = Me, Bu, and Ph). I with
oxalyl chloride gave QCOCOQ and QCH2COQ. I with PCl3 gave Q3P. I with POCl3 gave Q2P(O)OH. I with S2Cl2 and
SOCl2 gave Q2S and Q2SO, resp.
Indexing
Heterocyclic Compounds (More Than One Hetero Atom) (Section 28)
Concepts
Acid chlorides
reaction of, by 4-lithio-3-phenylsydnone
Reactant; Reactant or reagent
SciFinder Page 64
Substances
13973-33-6P
16796-16-0P
16796-20-6P
16796-22-8P
16796-23-9P
16796-25-1P
16796-26-2P
16796-27-3P

16796-28-4P
16796-29-5P

prepn. of

Synthetic preparation; Preparation


3668-24-4

reaction with acid chlorides

Reactant; Reactant or reagent


Supplementary Terms
SYDNONES; PYRAZOLES
Tags
0 Tags
Comments
0 Comments

Copyright 2017 American Chemical Society (ACS). All Rights Reserved.

You might also like