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Cyclohexylamine

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Cyclohexylamine[1]
Names
IUPAC name
Cyclohexanamine
Other names
Aminocyclohexane
Aminohexahydrobenzene
Hexahydroaniline
Identifiers
3D model (JSmol)
ChEBI
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
Acidity (pKa) 10.64[2]
1.4565
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. gasolineInstability 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)
Lethal dose or concentration (LD, LC):
156 mg/kg (rat, oral)
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.

Preparation

Cyclohexylamine is produced by two routes, the main one being hydrogenation of aniline using cobalt or nickel catalysts:[3]

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 is derived from cyclohexylamine.[3]

Toxicity

LD50 (rat; p.o.) = 0.71 ml/kg[4]

Safety

It is flammable, with flash point at 28.6 °C. It is toxic by both ingestion and inhalation; the inhalation itself may be fatal. It readily absorbs through skin, which it irritates. 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.[5]

References

  1. ^ Merck Index, 11th Edition, 2735.
  2. ^ H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.
  3. ^ a b Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
  4. ^ The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.
  5. ^ Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix. {{cite book}}: Cite has empty unknown parameter: |coauthors= (help)