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Cyclohexylamine^[1]
Names
	Preferred IUPAC name Cyclohexanamine
	Other names Aminocyclohexane; Aminohexahydrobenzene; Hexahydroaniline; Hexahydrobenzenamine
Identifiers
CAS Number	108-91-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15773 ;
ChEMBL	ChEMBL1794762;
ChemSpider	7677 ;
ECHA InfoCard	100.003.300
EC Number	203-629-0;
IUPHAR/BPS	5507;
KEGG	C00571 ;
PubChem CID	7965;
RTECS number	GX0700000;
UNII	I6GH4W7AEG ;
CompTox Dashboard (EPA)	DTXSID1023996 ;
	InChI InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 Key: PAFZNILMFXTMIY-UHFFFAOYSA-N ; InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 Key: PAFZNILMFXTMIY-UHFFFAOYAP;
	SMILES NC1CCCCC1;
Properties
Chemical formula	C6H13N
Molar mass	99.17
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
Vapor pressure	11 mmHg (20°C)
Acidity (pKa)	10.64
Refractive index (nD)	1.4565
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H312, H314, H361
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P322, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)	3 3 0
Flash point	28.6 °C (83.5 °F; 301.8 K)
Autoignition; temperature	293 °C (559 °F; 566 K)
Explosive limits	1.5–9.4%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	156 mg/kg (rat, oral)
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 10 ppm (40 mg/m3)
IDLH (Immediate danger)	N.D.
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 (e.g. cyclamate)

Preparation

Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of aniline using some cobalt- or nickel-based catalysts:^[4]

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. The amine itself is an effective corrosion inhibitor. It has been used as a flushing aid in the printing ink industry.^[5]

Drugs List

It is a building block for pharmaceuticals (e.g., mucolytics, analgesics, and bronchodilators). Most of the drugs in the following list fall into the arena of sulfonamide hypoglycemics though:

Acetohexamide
Amesergide
Bromhexine
Brovanexine
CGP-11112 (not actually made from CyNH2 but CyN containing).
Cilostazol
Clorexolone
Cyclamate
Enpromate
Esaprazole
Glibenclamide
Glicaramide
Gliquidone
Glipizide
Glisindamide
Glisolamide
Glycyclamide
Glyhexamide
Hexazinone
Hexylcaine
Hydroxyhexamide
lomustine
Metahexamide
Timegadine
Thiohexamide
U-37883A

Toxicity

Cyclohexylamine has a low acute toxicity with LD₅₀ (rat; p.o.) = 0.71 ml/kg^[6] Like other amines, 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. 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.^[2]

References

^ Merck Index, 11th Edition, 2735.
^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0168". National Institute for Occupational Safety and Health (NIOSH).
^ H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.
^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527306732.
^ Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix.
^ The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.