1412. α-Bromobenzyl Cyanide

Nomenclature

CAS number: 5798-79-8
α-Bromobenzeneacetonitrile; α-bromophenylacetonitrile; α-bromo-α-tolunitrile; B.B.C.; C.A.; Camite.
C8H6BrN; mol wt 196.04.
C 49.01%, H 3.08%, Br 40.76%, N 7.14%.

Description and references

The practical industrial prepn consists of three steps: (1) Chlorination of toluene to form benzyl chloride, (2) conversion of benzyl chloride to benzyl cyanide by the action of sodium cyanide in alcoholic soln, (3) bromination of the benzyl cyanide with bromine vapor in the presence of sunlight: Steinkopf et al., Ber. 53, 1146 (1920); Nekrassov, J. Prakt. Chem. 119, 108 (1928).

Chemical structure

Properties

Crystalline mass, mp 29°. Odor of soured fruit. bp760 242° (dec); bp12 132-134°. d429 1.539. Vapor density 6.8 (air = 1). Vapor pressure at 20° = 0.012 mm; at 30° = 0.028 mm. Slightly sol in water. Freely sol in alcohol, ether, chloroform, acetone, and other common organic solvents; also sol in phosgene, chloropicrin, benzyl cyanide. LC (30 min.): 0.90 mg/l (A. M. Prentiss, Chemicals in War (McGraw-Hill, New York, 1937) p 141).

Caution

Highly potent lacrimator. See Patty's Industrial Hygiene and Toxicology vol. 2D, G. D. Clayton, F. E. Clayton, Eds. (Wiley-Interscience, New York, 4th ed., 1994) p 3163.

Use

War gas.