Cyclohexylamine

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Cyclohexylamine[1]
Cyclohexylamine-2D-skeletal.png
Cyclohexylamine-3D-balls.png
Names
Preferred IUPAC name
Cyclohexanamine
Other names
Aminocyclohexane
Aminohexahydrobenzene
Hexahydroaniline
Hexahydrobenzenamine
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.300 Edit this at Wikidata
EC Number
  • 203-629-0
KEGG
RTECS number
  • GX0700000
UNII
  • InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 checkY
    Key: PAFZNILMFXTMIY-UHFFFAOYSA-N checkY
  • InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
    Key: PAFZNILMFXTMIY-UHFFFAOYAP
  • NC1CCCCC1
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 labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
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)
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).
checkY verify (what is checkY☒N ?)

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[edit]

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[edit]

Cyclamate, a derivative of cyclohexylamine, is a popular artificial sweetener.

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]

Toxicity[edit]

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[edit]

  1. ^ Merck Index, 11th Edition, 2735.
  2. ^ a b c d e f 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. ^ a b 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. ^ Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix.
  6. ^ The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.