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Cyclohexylamine 1

Cyclohexylamine

Cyclohexylamine[1]

Identifiers

CAS number [2]


108-91-8  

PubChem [3]
7965

ChemSpider [4]
7677  

UNII [5]
I6GH4W7AEG  

EC number [6]
203-629-0

KEGG [7]
C00571  

ChEBI [8]
CHEBI:15773  

RTECS number GX0700000

Jmol-3D images [9]


Image 1

Properties

Molecular formula C6H13N

Molar mass 99.17 g mol−1

Appearance clear to yellowish liquid

Odor strong, fishy, amine odor

Density 0.8647 g/cm3

Melting point −17.7 °C (0.1 °F; 255.5 K)

Boiling point 134.5 °C (274.1 °F; 407.6 K)

Solubility in water Miscible

Solubility very soluble in ethanol, oil


miscible in ethers, acetone, esters, alcohol, ketones

Acidity (pKa) [10]


10.64

Refractive index (nD) 1.4565


Cyclohexylamine 2

Hazards

S-phrases S36 S37 S39

R/S statement R21 R23 R25 R36 R37 R38 R41

NFPA 704

Flash point 28.6 °C (83.5 °F; 301.8 K)

LD50 156 mg/kg (rat, oral)

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

[11]
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Infobox references

Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although
like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like
other amines, it is a weak base, compared to strong bases such as NaOH, but it is a stronger base than its aromatic
analog, aniline.
It is a useful intermediate in the production of many other organic compounds. It is a metabolite of cyclamate.

Preparation
Cyclohexylamine is produced by two routes, the main one being hydrogenation of aniline using cobalt or nickel
catalysts:[12]
C6H5NH2 + 3 H2 → C6H11NH2
It is also prepared by alkylation of ammonia using cyclohexanol.

Applications
Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to
sulfenamide-based reagents used as accelerators for vulcanization. It is a building block for pharmaceuticals (e.g.,
mucolytics, analgesics, and bronchodilators). The amine itself is an effective corrosion inhibitor. Some sweeteners
are derived from this amine, notably cyclamate. The herbicide hexazinone is derived from cyclohexylamine.

Toxicity
LD50 (rat; p.o.) = 0.71 ml/kg[13]

Safety
It is flammable, with flash point at 28.6 °C. It is toxic by both ingestion and inhalation; the inhalation itself may be
fatal. It readily absorbs through skin, which it irritates. It is corrosive. Cyclohexylamine is listed as an extremely
hazardous substance as defined by Section 302 of the U.S. Emergency Planning and Community Right-to-Know
Act. It has been used as a flushing aid in the printing ink industry.
In regards to occupational exposures, the National Institute for Occupational Safety and Health has suggested
workers not be exposed to a recommended exposure limit of over 10 ppm (40 mg/m3) over an eight hour workshift.
Cyclohexylamine 3

References
[1] Merck Index, 11th Edition, 2735.
[2] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=108-91-8
[3] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=7965
[4] http:/ / www. chemspider. com/ Chemical-Structure. 7677. html
[5] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=I6GH4W7AEG
[6] http:/ / esis. jrc. ec. europa. eu/ lib/ einecs_IS_reponse. php?genre=ECNO& entree=203-629-0
[7] http:/ / www. kegg. jp/ entry/ C00571
[8] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=15773
[9] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=NC1CCCCC1
[10] H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.
[11] http:/ / en. wikipedia. org/ w/ index. php?title=Special:ComparePages& rev1=449888458& page2=Cyclohexylamine
[12] Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry,
Wiley-VCH, Weinheim, 2005.
[13] The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.
Article Sources and Contributors 4

Article Sources and Contributors


Cyclohexylamine  Source: http://en.wikipedia.org/w/index.php?oldid=601795272  Contributors: A876, Author2010, Beetstra, Benjah-bmm27, Bjohns86, Chem-awb, ChemNerd, Christian75,
DMacks, DePiep, Drphilharmonic, Edgar181, HaniballCartho, JZNIOSH, Jeremy334, Josh Parris, Marcosm21, NReitzel, Reyk, Romney, Shaddack, Smokefoot, Thricecube, Xprofj, Zombiejesus,
13 anonymous edits

Image Sources, Licenses and Contributors


File:Cyclohexylamine-2D-skeletal.png  Source: http://en.wikipedia.org/w/index.php?title=File:Cyclohexylamine-2D-skeletal.png  License: Public Domain  Contributors: Benjah-bmm27,
Mrgreen71
File:Cyclohexylamine-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Cyclohexylamine-3D-balls.png  License: Public Domain  Contributors: Ben Mills
File:Yes check.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Yes_check.svg  License: Public Domain  Contributors: Anomie
File:X mark.svg  Source: http://en.wikipedia.org/w/index.php?title=File:X_mark.svg  License: Public Domain  Contributors: User:Gmaxwell

License
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