omega-Chloroacetophenone
Title: w-Chloroacetophenone
CAS Registry Number: 532-27-4
CAS Name: 2-Chloro-1-phenylethanone
Additional Names: 2-chloroacetophenone; a-chloroacetophenone; phenacyl chloride; Chemical Mace; CN
Molecular Formula: C8H7ClO
Molecular Weight: 154.59
Percent Composition: C 62.16%, H 4.56%, Cl 22.93%, O 10.35%
Line Formula: C6H5COCH2Cl
Literature 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).
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).
Melting point: mp 58-59°; also reported as 54° (Macy) and 56.5° (Rheinboldt, Perrier)
Boiling point: bp 244-245°
Density: d15 1.324
Toxicity data: 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.

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