Chemistry:Chloroacetyl chloride
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| Names | |
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| Preferred IUPAC name
Chloroacetyl chloride | |
| Other names
2-Chloroacetyl chloride
Chloroacetic acid chloride Chloroacetic chloride Monochloroacetyl chloride | |
| Identifiers | |
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| UNII | |
| UN number | 1752 |
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| 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 |    
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| GHS Signal word | Danger |
| 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 | |
| NFPA 704 (fire diamond) | |
| Flash point | noncombustible [1] |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
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none[1] |
REL (Recommended)
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TWA 0.05 ppm (0.2 mg/m3)[1] |
IDLH (Immediate danger)
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N.D.[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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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]
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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]
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With anisole, it is used for the synthesis of venlafaxine.
In one patent, chloroacetyl chloride was used in the production of trianisylethylene [7109-27-5],[7] a compound with known estrogenic activity in its own right but is used as a precursor for Chlorotrianisene.
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.[8]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 NIOSH Pocket Guide to Chemical Hazards. "#0120". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0120.html.
- ↑ "OSHA Occupational Chemical Database". Occupational Safety and Health Administration (OSHA). https://www.osha.gov/chemicaldata/685.
- ↑ 3.0 3.1 Paul R. Worsham (1993). "15. Halogenated Derivatives". Acetic acid and its derivatives. New York: M. Dekker. pp. 288–298. ISBN 0-8247-8792-7. https://books.google.com/books?id=3MjdGp1v1YIC&pg=RA2-PA288.
- ↑ Robert H. Baker and Frederick G. Bordwell (1955). "tert-Butyl acetate". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv3p0141.; Collective Volume, 3
- ↑ T. J. Reilly (1999). "The Preparation of Lidocaine". J. Chem. Educ. 76 (11): 1557. doi:10.1021/ed076p1557. Bibcode: 1999JChEd..76.1557R. http://jchemed.chem.wisc.edu/Journal/Issues/1999/Nov/abs1557.html.
- ↑ Nathan Levin and Walter H. Hartung (1955). "ω-Chloroisonitrosoacetophenone". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv3p0191.; Collective Volume, 3, pp. 191
- ↑ Г. Хухр нский Л. Н. Волове льский, SU213825 ().
- ↑ "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevention. 2011. https://www.cdc.gov/niosh/npg/npgd0120.html.
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