Chloroacetyl chloride

Chloroacetyl chloride
Names
IUPAC name
chloroacetyl chloride
Other names
Chloroacetic acid chloride, Chloroacetic chloride, Monochloroacetyl chloride
Identifiers
79-04-9 N
ChemSpider 13856283 N
EC Number 201-171-6
Jmol interactive 3D Image
KEGG C14859 YesY
PubChem 6577
Properties
C2H2Cl2O
Molar mass 112.94 g·mol−1
Appearance Colorless to yellow liquid
Density 1.42 g/mL
Melting point −22 °C (−8 °F; 251 K)
Boiling point 106 °C (223 °F; 379 K)
Reacts
Vapor pressure 19 mmHg (20°C)[1]
Hazards
Safety data sheet Oxford MSDS
T N C
Flash point noncombustible [1]
US health exposure limits (NIOSH):
none[1]
TWA 0.05 ppm (0.2 mg/m3)[1]
N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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.[2] 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[3] 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:[4]

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.[2] Phenacyl chloride is synthesized in a Friedel-Crafts acylation of benzene, with an aluminium chloride catalyst:[5]

Safety

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

There is no regulated permissible exposure limit set by the Occupational Safety and Health Administration. However, the National Institute for Occupational Safety and Health has set a recommended exposure limit at 0.05 ppm over an eight-hour work day.[6]

References

  1. 1 2 3 4 5 "NIOSH Pocket Guide to Chemical Hazards #0120". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 Paul R. Worsham (1993). "15. Halogenated Derivatives". In Zoeller, Joseph R.; Agreda, V. H., eds. Acetic acid and its derivatives (Google Books excerpt). New York: M. Dekker. pp. 288–298. ISBN 0-8247-8792-7.
  3. ↑ Robert H. Baker and Frederick G. Bordwell (1955). "tert-Butyl acetate". Org. Synth.; Coll. Vol. 3
  4. ↑ T. J. Reilly (1999). "The Preparation of Lidocaine". J. Chem. Ed. 76 (11): 1557. doi:10.1021/ed076p1557.
  5. ↑ Nathan Levin and Walter H. Hartung (1955). "ω-Chloroisonitrosoacetophenone". Org. Synth.; Coll. Vol. 3, p. 191
  6. ↑ "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevention. 2011.

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