Chloroacetyl chloride
| Skeletal formula | |
| ball-and-stick model | |
| Names | |
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| IUPAC name
chloroacetyl chloride
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| Other names
Chloroacetic acid chloride, Chloroacetic chloride, Monochloroacetyl chloride
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| Identifiers | |
79-04-9  |
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| ChemSpider | 13856283  |
| EC Number | 201-171-6 |
| Jmol 3D model | Interactive image |
| KEGG | C14859 |
| PubChem | 6577 |
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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] |
| Vapor pressure | {{{value}}} |
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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.[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
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