Chloroacetonitrile Explained

Chloroacetonitrile is the organic compound with the formula ClCH₂CN. A colorless liquid, it is derived from acetonitrile (CH₃CN) by replacement of one H with Cl. In practice, it is produced by dehydration of chloroacetamide.^[1] The compound is an alkylating agent,^[2] and as such is handled cautiously.

Chloroacetonitrile is also generated in situ by the reaction of acetonitrile with sulfur monochloride. A second chlorination gives dichloroacetonitrile, which undergoes cycloaddition with sulfur monochloride to give 4,5-dichloro-1,2,3-dithiazolium chloride:^[3]

Cl₂CHCN + S₂Cl₂ → [S₂NC₂Cl₂]Cl + HCl

References

1. D. B.. Reisner. E. C. . Horning. 10.15227/orgsyn.030.0022. Chloroacetonitrile. Organic Syntheses. 1950. 30. 22.
2. 10.15227/orgsyn.086.0001. Preparation of (3,5-Dimethoxy-1-Phenyl-Cyclohexa-2,5-Dienyl)-Acetonitrile Through Birch Reductive Alkylation (BRA). Organic Syntheses. 2009. 86. 1. Raphaël. Lebeuf. Muriel . Berlande. Frédéric. Robert. Yannick. Landais. free.
3. 10.1002/jhet.5570290306. Polysulfur-Nitrogen Heterocyclic Chemistry. 1992. Rees. Charles W.. Journal of Heterocyclic Chemistry. 29. 3. 639–651.

See also

• halogenation