Cyclohexylamine

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.

Cyclohexylamine[1]
Names
IUPAC name
Cyclohexanamine
Other names
Aminocyclohexane
Aminohexahydrobenzene
Hexahydroaniline
Hexahydrobenzenamine
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.300
EC Number
  • 203-629-0
KEGG
RTECS number
  • GX0700000
UNII
Properties
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)
Miscible
Solubility very soluble in ethanol, oil
miscible in ethers, acetone, esters, alcohol, ketones
Vapor pressure 11 mmHg (20° C)[2]
Acidity (pKa) 10.64[3]
1.4565
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H226, H302, H312, H314, H361
P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P308+313, P310, P312, P321, P322, P330
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point 28.6 °C (83.5 °F; 301.8 K)
293 °C (559 °F; 566 K)
Explosive limits 1.5–9.4%[2]
Lethal dose or concentration (LD, LC):
156 mg/kg (rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 10 ppm (40 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 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. 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 and the anesthetic hexylcaine are derived from cyclohexylamine.[4]

Toxicity

LD50 (rat; p.o.) = 0.71 ml/kg[5]

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.[6]

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]

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References
  1. Merck Index, 11th Edition, 2735.
  2. NIOSH Pocket Guide to Chemical Hazards. "#0168". National Institute for Occupational Safety and Health (NIOSH).
  3. H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.
  4. 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.
  5. The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.
  6. Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix.
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