Chloroacetyl chloride

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

Chloroacetyl chloride
Names
Preferred IUPAC name
Chloroacetyl chloride
Other names
2-Chloroacetyl chloride
Chloroacetic acid chloride
Chloroacetic chloride
Monochloroacetyl chloride
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.065
EC Number
  • 201-171-6
KEGG
RTECS number
  • AO6475000
UNII
UN number 1752
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
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H301, H311, H314, H331, H372, H400
P260, P261, P264, P270, P271, P273, P280, P301+310, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+233, P405
Flash point noncombustible [1]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 TWA 0.05 ppm (0.2 mg/m3)[1]
IDLH (Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Not to be confused with Acetyl chloride or Chloroacetic acid.

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 herbicides in the chloroacetanilide family including metolachlor, acetochlor, 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]

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gollark: Indeed.
gollark: Besides, under a sane T&C that'd be covered by hacking/malicious whatevers.
gollark: Hopefully TJ09'd use SSH keys and not a password anyway.
gollark: Brute-forcing "site code stuff" I have no clue.

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0120". National Institute for Occupational Safety and Health (NIOSH).
  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". Organic Syntheses.; Collective Volume, 3
  4. T. J. Reilly (1999). "The Preparation of Lidocaine". J. Chem. Educ. 76 (11): 1557. doi:10.1021/ed076p1557.
  5. Nathan Levin and Walter H. Hartung (1955). "ω-Chloroisonitrosoacetophenone". Organic Syntheses.; Collective Volume, 3, p. 191
  6. "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevention. 2011.
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