Cyclohexylamine
Names | |
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Preferred IUPAC name
Cyclohexanamine | |
Other names
Aminocyclohexane
Aminohexahydrobenzene Hexahydroaniline Hexahydrobenzenamine | |
Identifiers | |
3D model (
JSmol ) |
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3DMet | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.003.300 |
EC Number |
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IUPHAR/BPS |
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KEGG | |
PubChem CID
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RTECS number
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UNII | |
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
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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) |
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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Cyclohexylamine is an
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
printing ink industry.[5]
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.
- ^ 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.