Phenacyl chloride

Phenacyl chloride is an organic compound with the formula C6H5C(O)CH2Cl. This colourless solid is a powerful lachrymator as well as a useful precursor to other organic compounds.

Structure and reactivity

Phenacyl chloride is a chloro ketone that is acetophenone in which the methyl group has been replaced by a chlorine atom. It is a member of acetophenones and a chloro ketone. It derives from an acetophenone.

Synthesis

Phenacyl chloride can be prepared by chlorination of acetophenone: C6H5C(O)CH3 + Cl2 → C6H5C(O)CH2Cl + HCl The reaction is performed in the presence of ultraviolet light.

Uses

Phenacyl chloride is used as a chemical intermediate in the manufacture of pharmaceuticals, herbicides, fungicides, dyes, and plasticizers. It is also used in the Knoevenagel condensation to give the corresponding phenacyl ester.

Safety

Phenacyl chloride is a powerful lachrymator, as is the case with other acyl chlorides. It is also a skin irritant.

See also

• Acyl chloride
• Lachrymatory agent
• Knoevenagel condensation

References

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