Chloroacetyl chloride

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

Not to be confused with Acetyl chloride or Chloroacetic acid.
Chloroacetyl chloride
Skeletal formula
ball-and-stick model
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
  • InChI=1S/C2H2Cl2O/c3-1-2(4)5/h1H2 ☒N
    Key: VGCXGMAHQTYDJK-UHFFFAOYSA-N ☒N
  • InChI=1/C2H2Cl2O/c3-1-2(4)5/h1H2
    Key: VGCXGMAHQTYDJK-UHFFFAOYAB
  • C(C(=O)Cl)Cl
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
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H311, H314, H331, H372, H400
P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamond
3
0
1
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]
Safety data sheet (SDS) Oxford MSDS
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

Production

Industrially, it is produced by the carbonylation of methylene chloride, oxidation of vinylidene chloride, or the addition of chlorine to ketene.[3] 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[4] 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:[5]

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.[3] Phenacyl chloride is synthesized in a Friedel-Crafts acylation of benzene, with an aluminium chloride catalyst:[6]

With anisole, it is used for the synthesis of venlafaxine.

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.[7]

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0120". National Institute for Occupational Safety and Health (NIOSH).
  2. "OSHA Occupational Chemical Database". Occupational Safety and Health Administration (OSHA).
  3. Paul R. Worsham (1993). "15. Halogenated Derivatives" (Google Books excerpt). In Zoeller, Joseph R.; Agreda, V. H. (eds.). Acetic acid and its derivatives. New York: M. Dekker. pp. 288–298. ISBN 0-8247-8792-7.
  4. Robert H. Baker and Frederick G. Bordwell (1955). "tert-Butyl acetate". Organic Syntheses.; Collective Volume, vol. 3
  5. T. J. Reilly (1999). "The Preparation of Lidocaine". J. Chem. Educ. 76 (11): 1557. Bibcode:1999JChEd..76.1557R. doi:10.1021/ed076p1557.
  6. Nathan Levin and Walter H. Hartung (1955). "ω-Chloroisonitrosoacetophenone". Organic Syntheses.; Collective Volume, vol. 3, p. 191
  7. "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevention. 2011.
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