Chloroacetyl chloride

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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 Edit this at Wikidata
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
Safety data sheet (SDS) Oxford MSDS
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word
 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)
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]
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

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.[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]

Synthesis of lidocaine.png

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]

Preparation of phenacyl chloride.png

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. ^ a b c d e 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. ^ a b 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, 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, 3, p. 191
  7. ^ "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevention. 2011.
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