1109. Benzotrichloride

Nomenclature

CAS number: 98-07-7
(Trichloromethyl)benzene; α,α,α-trichlorotoluene; phenylchloroform; ω,ω,ω-trichlorotoluene; benzenyl trichloride; toluene trichloride.
C7H5Cl3; mol wt 195.47.
C 43.01%, H 2.58%, Cl 54.41%.

Description and references

Produced by chlorination of boiling toluene in the presence of light and of 2% phosphorus trichloride: Swarts, Bull. Soc. Chim. Belg. 31, 375 (1922); Conklin, US 1828858; US 1828859 (both 1931 to Solvay Process Co.). Commercial grades may contain hydrochloric acid, benzylidene chloride, and benzyl chloride. Purification procedures: Holleman, deMooy, Rec. Trav. Chim. 33, 25, 33 (1914); Britton, US 1804458 (1931 to Dow); Chem. Zentralbl. 1931, II, 497. Toxicity data: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951). Review: H. C. Lin in Kirk-Othmer Encyclopedia of Chemical Technology vol. 6 (John Wiley & Sons, New York, 4th ed., 1993) pp 113-126.

Chemical structure

Properties

Colorless, oily liquid with pungent odor. Fumes in air. mp -5.0°. d420 1.3756. bp760 220.8°. bp60 129°; bp25 105°; bp10 89°. nD20 1.55789. Autoignition temp: 211°. Unstable. Corrosive. Hydrolyzes in the presence of moisture, forming benzoic and hydrochloric acids. Insol in water. Sol in alcohol, benzene, ether, many other organic solvents. LD50 orally in rats: 6.0 g/kg (Smyth).

Caution

Vapors may be stongly irritanting and lacrimatory (Lin). This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-31.

Use

In dye chemistry. In organic syntheses (source of benzenyl group).