Structural Formula Vector Image
Title: Cyclohexylamine
CAS Registry Number: 108-91-8
CAS Name: Cyclohexanamine
Additional Names: aminocyclohexane; hexahydroaniline
Molecular Formula: C6H13N
Molecular Weight: 99.17
Percent Composition: C 72.67%, H 13.21%, N 14.12%
Literature References: Prepd by the catalytic hydrogenation of aniline at elevated temps and pressures. Fractionation of the crude reaction product yields cyclohexylamine, unchanged aniline, and a high-boiling residue contg N-phenylcyclohexylamine (cyclohexylaniline) and dicyclohexylamine. Review and bibliography: Carswell, Morrill, Ind. Eng. Chem. 29, 1247 (1937). Toxicity data: H. F. Smyth et al., Am. Ind. Hyg. Assoc. J. 30, 470 (1969).
Properties: Liquid. Strong, fishy, amine odor. d2525 0.8647. mp -17.7°. bp760 134.5°; bp500 118.9°; bp300 102.5°; bp100 72.0°; bp50 56.0°; bp30 45.1°; bp25 41.3°; bp20 36.4°; bp15 30.5°. nD25 1.4565. Strong base. Completely misc with water and with common organic solvents, including alcohols, ethers, ketones, esters, aliphatic hydrocarbons, aromatic hydrocarbons and their chlorinated derivatives. On distillation with water, cyclohexylamine forms an azeotropic mixture contg 44.2% cyclohexylamine by weight, bp760 96.4°. Reacts with excess ammonia and zinc chloride at 350° to produce a-picoline: Nordt, Conversion of Hexahydroaniline into Pyridine Bases, Off. Pub. Bd., Report PB 704 (1941). LD50 orally in rats: 0.71 ml/kg (Smyth).
Melting point: mp -17.7°
Boiling point: bp760 134.5°; bp500 118.9°; bp300 102.5°; bp100 72.0°; bp50 56.0°; bp30 45.1°; bp25 41.3°; bp20 36.4°; bp15 30.5°; bp760 96.4°
Index of refraction: nD25 1.4565
Density: d2525 0.8647
Toxicity data: LD50 orally in rats: 0.71 ml/kg (Smyth)
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin, mucous membranes, respiratory system; eye, skin burns; skin sensitization; cough, pulmonary edema; drowsiness, lightheadedness, dizziness; diarrhea, nausea, vomiting. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 84.
Use: In organic synthesis, manuf insecticides, plasticizers, corrosion inhibitors, rubber chemicals, dyestuffs, emulsifying agents, dry-cleaning soaps, acid gas absorbents.

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