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Cyclohexylamine 1




CAS number [2]


PubChem [3]

ChemSpider [4]

UNII [5]

EC number [6]

KEGG [7]

ChEBI [8]

RTECS number GX0700000

Jmol-3D images [9]

Image 1


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]


Refractive index (nD) 1.4565

Cyclohexylamine 2


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)

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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.

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

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.

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

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

[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:  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:  License: Public Domain  Contributors: Benjah-bmm27,
File:Cyclohexylamine-3D-balls.png  Source:  License: Public Domain  Contributors: Ben Mills
File:Yes check.svg  Source:  License: Public Domain  Contributors: Anomie
File:X mark.svg  Source:  License: Public Domain  Contributors: User:Gmaxwell

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