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.
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Preferred IUPAC name
Cyclohexanamine | |
Other names
Aminocyclohexane
Aminohexahydrobenzene Hexahydroaniline Hexahydrobenzenamine | |
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3D model (JSmol)
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3DMet |
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ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.003.300 |
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KEGG |
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CompTox Dashboard (EPA)
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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] |
Refractive index (nD)
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1.4565 |
Hazards | |
GHS labelling: | |
Danger | |
H226, H302, H312, H314, H361 | |
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) | |
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): | |
LD50 (median dose)
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156 mg/kg (rat, oral) |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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none[2] |
REL (Recommended)
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TWA 10 ppm (40 mg/m3)[2] |
IDLH (Immediate danger)
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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
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It is a useful intermediate in the production of many other organic compounds (e.g. cyclamate)
Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of aniline using some cobalt- or nickel-based catalysts:[4]
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. The herbicide hexazinone and the anesthetic hexylcaine are derived from cyclohexylamine.[4] It has been used as a flushing aid in the printing ink industry.[5]
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]