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Chloroacetyl chloride

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Chloroacetyl chloride
Skeletal formula
ball-and-stick model
Names
IUPAC name chloroacetyl chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.065 Edit this at Wikidata
EC Number
  • 201-171-6
KEGG
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • C(C(=O)Cl)Cl
Properties
Chemical formula C2H2Cl2O
Molar mass 112.94 g·mol
Appearance Colorless liquid
Density 1.42 g/mL
Melting point −22 °C (−8 °F; 251 K)
Boiling point 106 °C (223 °F; 379 K)
Solubility in water Reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Chloroacetyl chloride is a chlorinated acyl chloride. It is a bifunctional compound, making it a useful building block chemical.

Production

Industrially, it is produced by the carbonylation of methylene chloride, oxidation of vinylidene chloride, or the addition of chlorine to ketene. It may be prepared from chloroacetic acid and thionyl chloride, phosphorus pentachloride, or phosgene.

Reactions

Chloroacetyl chloride is bifunctional—the acyl chloride easily forms esters and amides, while the other end of the molecule is able to form other linkages, e.g. with amines. The use of chloroacetyl chloride in the synthesis of lidocaine is illustrative:

Applications

The major use of chloroacetyl chloride is as an intermediate in the production of alachlor and butachlor; an estimated 100 million pounds are used annually. Some chloroacetyl chloride is also used to produce phenacyl chloride, another chemical intermediate, also used as a tear gas. Phenacyl chloride is synthesized in a Friedel-Crafts acylation of benzene, with an aluminium chloride catalyst:

Safety

Like other acyl chlorides, reaction with other protic compounds such as amines, alcohols, and water generates hydrochloric acid, making it a lachrymator.

References

  1. ^ Paul R. Worsham (1993). "15. Halogenated Derivatives". In Zoeller, Joseph R.; Agreda, V. H., eds. (ed.). Acetic acid and its derivatives (Google Books excerpt). New York: M. Dekker. pp. 288–298. ISBN 0-8247-8792-7. {{cite book}}: |editor= has generic name (help)CS1 maint: multiple names: editors list (link)
  2. Robert H. Baker and Frederick G. Bordwell (1955). "tert-Butyl acetate". Organic Syntheses; Collected Volumes, vol. 3.
  3. T. J. Reilly (1999). "The Preparation of Lidocaine". J. Chem. Ed. 76 (11): 1557. doi:10.1021/ed076p1557.
  4. Nathan Levin and Walter H. Hartung (1955). "ω-Chloroisonitrosoacetophenone". Organic Syntheses; Collected Volumes, vol. 3, p. 191.
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