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IUPAC name chloroacetyl chloride | |
Identifiers | |
CAS Number | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.001.065 |
EC Number |
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KEGG | |
PubChem CID | |
CompTox Dashboard (EPA) | |
SMILES
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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). Y verify (what is ?) Infobox references |
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
- ^ 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) - Robert H. Baker and Frederick G. Bordwell (1955). "tert-Butyl acetate". Organic Syntheses; Collected Volumes, vol. 3.
- T. J. Reilly (1999). "The Preparation of Lidocaine". J. Chem. Ed. 76 (11): 1557. doi:10.1021/ed076p1557.
- Nathan Levin and Walter H. Hartung (1955). "ω-Chloroisonitrosoacetophenone". Organic Syntheses; Collected Volumes, vol. 3, p. 191.