Cyclohexylamine

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.
Cyclohexylcarbinol Cycloleucine Cyclomethycaine Cyclonite Cyclonium Iodide

Cyclohexylamine[1]
Cyclohexylamine-2D-skeletal.png
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Identifiers
CAS number 108-91-8 YesY
PubChem 7965
ChemSpider 7677 YesY
UNII I6GH4W7AEG YesY
EC number 203-629-0
KEGG C00571 YesY
ChEBI CHEBI:15773 YesY
RTECS number GX0700000
Jmol-3D images Image 1
Properties
Molecular formula C6H13N
Molar mass 99.17 g mol−1
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[2]
Refractive index (nD) 1.4565
Hazards
S-phrases S36 S37 S39
R/S statement R21 R23 R25 R36 R37 R38 R41
NFPA 704
NFPA 704.svg
3
3
0
Flash point 28.6 °C; 83.5 °F; 301.8 K
Autoignition temperature 293 °C; 559 °F; 566 K
LD50 156 mg/kg (rat, oral)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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. It is a metabolite of cyclamate.