Chloroacetophenone


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chloroacetophenone

[¦klȯr·ō‚as·ə′tä·fə‚nōn]
(organic chemistry)
C6H5COCH2Cl Rhombic crystals melting at 59°C; an intermediate in organic synthesis.

Chloroacetophenone

 

C6H5C(O)CH2Cl, a compound obtained as colorless crystals, with a melting point of 59°C and a boiling point of 244°–245°C. Its volatility (maximum concentration) is 0.11 mg/liter at 20°C. A strong lacrimator, chloroacetophenone is poorly soluble in water but readily soluble in organic solvents. It is stable to hydrolysis; under cold conditions it practically does not hydrolyze, even in alkaline aqueous solutions. It reacts vigorously with alcohol solutions of Na2S, with the formation of nontoxic diphenacyl sulfide, (C6H5COCH2)2S. Chloroacetophenone is produced by the chlorination of acetophenone.

The minimal active concentration is 0.0001 mg/liter, and the intolerable concentration, 0.002 mg/liter (for 2 min). Gas masks provide protection against the effects of chloroacetophenone. Proposed as a poison at the end of World War I, chloroacetophenone has never been tested in combat.