Chlorobutanol

Chlorobutanol (trichloro-2-methyl-2-propanol) is a
preservative, sedative, hypnotic and weak local anesthetic similar
Chlorobutanol
in nature to chloral hydrate. It has antibacterial and antifungal
properties. Chlorobutanol is typically used at a concentration of
0.5% where it lends long term stability to multi-ingredient
formulations. However, it retains antimicrobial activity at 0.05%
in water. Chlorobutanol has been used in anesthesia and
euthanasia of invertebrates and fishes.[1][2] It is a white, volatile
solid with a camphor-like odor.
Names
Preferred IUPAC name
Contents 1,1,1-Trichloro-2-methylpropan-
2-ol
Synthesis Other names
Toxicity 1,1,1-Trichloro-2-methyl-2-
Parthenogenesis propanol; Chlorbutol; Chloreton;
Chloretone; Chlortran; Trichloro-
Pharmacology
tert-butyl alcohol; 1,1,1-Trichloro-
References
tert-butyl alcohol; 2-
External links (Trichloromethyl)propan-2-ol,
1,1,1-trichloro-2-methyl-2-
propanol; tert-Trichlorobutyl
Synthesis alcohol; Trichloro-tert-butanol;
Trichlorisobutylalcohol; 2,2,2-
Chlorobutanol was first Trichloro-1,1-dimethylethanol
synthesized in 1881 by
the German chemist Identifiers
Conrad Willgerodt (1841– CAS Number 57-15-8 (https://com
1930).[3] monchemistry.cas.or
g/detail?cas_rn=57-1
Chlorobutanol is formed
by the reaction of 5-8)
chloroform and acetone in 3D model Interactive image (htt
Sublimed crystals of chlorobutanol the presence of potassium (JSmol) ps://chemapps.stola
or sodium hydroxide. It f.edu/jmol/jmol.php?
may be purified by
model=ClC%28Cl%2
sublimation or recrystallisation.[4]
9%28Cl%29C%28
C%29%28C%29O)
Toxicity ChEMBL ChEMBL1439973 (ht
tps://www.ebi.ac.uk/c
hembldb/index.php/c
ompound/inspect/Ch
EMBL1439973)
Chlorobutanol is highly toxic to the liver, is a skin irritant and a ChemSpider 13842993 (https://w
severe eye irritant.[5] ww.chemspider.com/
Chemical-Structure.1
Parthenogenesis 3842993.html)
ECHA 100.000.288 (https://
Chlorobutanol has proven effective at stimulating parthenogenesis InfoCard echa.europa.eu/subs
in sea urchin eggs up to the pluteus stage, possibly by increasing
tance-information/-/s
irritability to cause stimulation. For the eggs of the fish Oryzias
ubstanceinfo/100.00
latipes, however, chlorobutanol only acted as an anesthetic.[6]
0.288)
EC Number 200-317-6
Pharmacology
KEGG D01942 (https://ww
It is an anesthetic with effects related to isoflurane and w.kegg.jp/entry/D019
halothane.[7] 42)
PubChem 5977 (https://pubche
References CID m.ncbi.nlm.nih.gov/c
ompound/5977)
1. W. N. McFarland & G. W. Klontz (1969). "Anesthesia in
fishes". Federation Proceedings. 28 (4): 1535–1540. UNII HM4YQM8WRC (htt
PMID 4894939 (https://pubmed.ncbi.nlm.nih.gov/48949 ps://fdasis.nlm.nih.go
39). v/srs/srsdirect.jsp?re
2. John E. Cooper (2011). "Anesthesia, analgesia, and gno=HM4YQM8WR
euthanasia of invertebrates" (https://doi.org/10.1093%2
C)
Filar.52.2.196). ILAR Journal. 52 (2): 196–204.
doi:10.1093/ilar.52.2.196 (https://doi.org/10.1093%2Fila CompTox DTXSID1041217 (htt
r.52.2.196). PMID 21709312 (https://pubmed.ncbi.nlm.n Dashboard ps://comptox.epa.go
ih.gov/21709312). (EPA)
v/dashboard/chemic
3. See: al/details/DTXSID10
Willgerodt, C. (1881). "Ueber die Einwirkung 41217)
ätzender Alkalien auf halogenirte Verbindungen in InChI
Acetonlösungen" (https://babel.hathitrust.org/cgi/pt?
InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)
id=hvd.cl1hzb&view=1up&seq=873) [On the action
7/h8H,1-2H3
of caustic alkalies on halogenated compounds in
Key: OSASVXMJTNOKOY-UHFFFA
acetone solutions]. Berichte der Deutschen
OYSA-N
Chemischen Gesellschaft (in German). 14 (2):
2451–2460. doi:10.1002/cber.188101402191 (http InChI=1/C4H7Cl3O/c1-3(2,8)4(5,6)
s://doi.org/10.1002%2Fcber.188101402191). 7/h8H,1-2H3
Key: OSASVXMJTNOKOY-UHFFFA
Willgerodt, C. (1882). "Ueberführung des OYAO
Acetonchloroforms in die Oxyisobuttersäure" (http
s://babel.hathitrust.org/cgi/pt?id=uiug.30112025692 SMILES
838&view=1up&seq=1205) [Conversion of ClC(Cl)(Cl)C(C)(C)O
chlorobutanol into 2-hydroxyisobutyric acid].
Berichte der Deutschen Chemischen Gesellschaft Properties
(in German). 15 (2): 2305–2308. Chemical C4H7Cl3O
doi:10.1002/cber.188201502176 (https://doi.org/10. formula
1002%2Fcber.188201502176).
Molar mass 177.45 g·mol−1
Willgerodt, C. (1883). "Zur Kenntniss des
Acetonchloroforms" (https://babel.hathitrust.org/cgi/ Appearance White solid
pt?id=osu.32435060218708&view=1up&seq=469) Odor Menthol
 [[Contribution] to [our] knowledge of chlorobutanol]. Melting point 95–99 °C (203–
Berichte der Deutschen Chemischen Gesellschaft 210 °F; 368–372 K)
(in German). 16 (2): 1585.
doi:10.1002/cber.18830160218 (https://doi.org/10.1 Boiling point 167 °C (333 °F;
002%2Fcber.18830160218). 440 K)
Willgerodt, C.; Genieser, Ad. (1888). "Beiträge zur Solubility in Slightly soluble
Kenntniss des Acetonchloroforms" (https://babel.hat water
hitrust.org/cgi/pt?id=mdp.39015026393622&view= Solubility in Soluble
1up&seq=377) [Contributions to [our] knowledge of acetone
chlorobutanol]. Journal für praktische Chemie (in
German). 37 (8): 361–374. Pharmacology
doi:10.1002/prac.18880370131 (https://doi.org/10.1 ATC code A04AD04 (WHO (htt
002%2Fprac.18880370131). ps://www.whocc.no/a
4. "Chlorobutanol" (http://www.sciencemadness.org/smwi tc_ddd_index/?code
ki/index.php/Chlorobutanol#Preparation). =A04AD04))
Sciencemadness Wiki. Retrieved 14 August 2020.
Hazards
5. MSDS (https://web.archive.org/web/20131106022221/
https://www.spectrumchemical.com/MSDS/C4046.PD Occupational safety and health
F) (OHS/OSH):
6. Embryologia 1956 (http://onlinelibrary.wiley.com/store/1 Main Xn
0.1111/j.1440-169X.1956.tb00062.x/asset/j.1440-169X. hazards
1956.tb00062.x.pdf?v=1&t=ie95071c&s=493f4ab23ad
NFPA 704
771e4d05dcc297f7bba0b3bcdebd0) 1
(fire diamond)
7. Nicholas P. Franks (2006). "Molecular targets 2 0
underlying general anaesthesia" (https://www.ncbi.nlm.
nih.gov/pmc/articles/PMC1760740). British Journal of
Pharmacology. 147 Suppl 1: S72–S81. Except where otherwise noted, data
doi:10.1038/sj.bjp.0706441 (https://doi.org/10.1038%2 are given for materials in their
Fsj.bjp.0706441). PMC 1760740 (https://www.ncbi.nlm. standard state (at 25 °C [77 °F],
nih.gov/pmc/articles/PMC1760740). PMID 16402123 (h 100 kPa).
ttps://pubmed.ncbi.nlm.nih.gov/16402123). verify (what is ?)
Infobox references
External links
Chlorobutanol MSDS (https://web.archive.org/web/20110716024512/http://siri.org/msds/f2/c
gc/cgchj.html)
A04AD04 (WHO (https://www.whocc.no/atc_ddd_index/?code=A04AD04))

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