Cyclohexylamine

Cyclohexylamine^[1]
Names
	IUPAC name Cyclohexanamine
	Other names Aminocyclohexane; Aminohexahydrobenzene; Hexahydroaniline
Identifiers
CAS Number	108-91-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15773 ;
ChemSpider	7677 ;
ECHA InfoCard	100.003.300
EC Number	203-629-0;
KEGG	C00571 ;
PubChem CID	7965;
RTECS number	GX0700000;
UNII	I6GH4W7AEG ;
CompTox Dashboard (EPA)	DTXSID1023996 ;
	InChI InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 Key: PAFZNILMFXTMIY-UHFFFAOYSA-N ; InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 Key: PAFZNILMFXTMIY-UHFFFAOYAP;
	SMILES NC1CCCCC1;
Properties
Chemical formula	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)
Solubility in water	Miscible
Solubility	very soluble in ethanol, oil ; miscible in ethers, acetone, esters, alcohol, ketones
Acidity (pKa)	10.64
Refractive index (nD)	1.4565
Hazards
NFPA 704 (fire diamond)	3 3 0
Flash point	28.6 °C (83.5 °F)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). verify (what is ?) Infobox references

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

^ Merck Index, 11th Edition, 2735.
^ H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.
^ ^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
^ The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.
^ Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix. {{cite book}}: Cite has empty unknown parameter: |coauthors= (help)

[1] Merck Index, 11th Edition, 2735.

[2] H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.

[Ullmann-3] 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.

[Apps-5] Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix. {{cite book}}: Cite has empty unknown parameter: |coauthors= (help)

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