Chloroacetyl chloride
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| Names | |
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Preferred IUPAC name
Chloroacetyl chloride
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| Other names
2-Chloroacetyl chloride
Chloroacetic acid chloride Chloroacetic chloride Monochloroacetyl chloride |
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| Identifiers | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.001.065 |
| EC Number | 201-171-6 |
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PubChem CID
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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) |
| Hazards | |
| Safety data sheet | Oxford MSDS |
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EU classification (DSD) (outdated)
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 T  N  C
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| Flash point | noncombustible |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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none |
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REL (Recommended)
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TWA 0.05 ppm (0.2 mg/m3) |
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IDLH (Immediate danger)
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N.D. |
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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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 (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.
Industrially, it is produced by the carbonylation of methylene chloride, oxidation of vinylidene chloride, or the addition of chlorine to ketene. It may be prepared from chloroacetic acid and thionyl chloride, phosphorus pentachloride, or phosgene.
Chloroacetyl chloride is bifunctional—the acyl chloride easily forms esters 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:
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.Phenacyl chloride is synthesized in a Friedel-Crafts acylation of benzene, with an aluminium chloride catalyst:
Like other acyl chlorides, reaction with other protic compounds such as amines, alcohols, and water generates hydrochloric acid, making it a lachrymator.
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