2115. ω-Chloroacetophenone

Nomenclature

CAS number: 532-27-4
2-Chloro-1-phenylethanone; 2-chloroacetophenone; α-chloroacetophenone; phenacyl chloride; Chemical Mace; CN.
C8H7ClO; mol wt 154.59.
C 62.16%, H 4.56%, Cl 22.93%, O 10.35%.

Description and references

Chemical warfare agent with lacrimatory properties. Prepn: R. Scholl, H. Korten, Ber. 34, 1902 (1901); H. Rheinboldt, M. Perrier, J. Am. Chem. Soc. 69, 3148 (1947); Schaefer, Sonnenberg, J. Org. Chem. 28, 1128 (1963). Purification: Lofton, US 2414418 (1947 to Pennsylvania Coal Prod.). Melting point determination and review of prepn: Macy, J. Chem. Educ. 24, 222 (1947). Comparative toxicity with o-chlorobenzylidenemalononitrile, q. v.: B. Ballantyne, D. W. Swanston, Arch. Toxicol. 40, 75 (1978).

Chemical structure

Properties

Crystals from dil alcohol, carbon tetrachloride, or light petr. mp 58-59°; also reported as 54° (Macy) and 56.5° (Rheinboldt, Perrier). bp 244-245°. d15 1.324. Vapor pressure at 20°: 5.4 × 10-3 mm Hg. Practically insol in water. Freely sol in alcohol, ether, benzene. LD50 in rats (mg/kg): 41 i.v., 36 i.p., 127 orally; LC50 in rats: 8750 mg/min/m3 (Ballantyne, Swanston).

Caution

Potential symptoms of overexposure are irritation of eyes, skin and respiratory system; pulmonary edema. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 60.

Use

Riot control agent.