Chloroacetone is a chemical compound with the formula CH3COCH2Cl. At STP it is a colorless liquid with a pungent odor.[3] On exposure to light, it turns to a dark yellow-amber color.[4] It was used as a tear gasinWorld War I.[5]
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| Names | |
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| Preferred IUPAC name
1-Chloropropan-2-one | |
| Other names
Acetonyl chloride, chloropropanone, 1-chloro-2-propanone, monochloroacetone, 1-chloro-2-ketopropane, 1-chloro-2-oxypropane | |
| Identifiers | |
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3D model (JSmol) |
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| 605369 | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.001.056 
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| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C3H5ClO | |
| Molar mass | 92.52 g·mol−1 |
| Appearance | Colorless liquid, oxidizes to amber |
| Density | 1.123 g/cm3 |
| Melting point | −44.5 °C (−48.1 °F; 228.7 K) |
| Boiling point | 119 °C (246 °F; 392 K) |
| 10 g/100 mL at 20 °C | |
| Solubility | miscible with alcohol, ether, chloroform |
| Vapor pressure | 1.5 kPa |
| -50.9·10−6cm3/mol | |
| 2.36 | |
| Hazards | |
| Flash point | 35 °C (95 °F; 308 K) |
| 610 °C (1,130 °F; 883 K) | |
| Explosive limits | 3.4% - ?[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
100 mg/kg (rats, oral)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Chloroacetone may be synthesized from the reaction between chlorine and diketene, or by the chlorination of acetone.
Chloroacetone is used to make dye couplers for colour photography, and is an intermediate in chemical manufacturing.[2] It is also used in the Feist-Benary synthesisoffurans.[6]
Chloroacetone purchased from commercial suppliers contains 5% impurities including mesityl oxide, which is not removed by distillation. Mesityl oxide can be oxidized using acidified KMnO4 to form a diol (followed by separation with ether), which is removed on subsequent distillation.[8]
Transportation of unstabilized chloroacetone has been banned in the United States by the US Department of Transportation. Stabilized chloroacetone is in hazard class 6.1 (Poison Inhalation Hazard). Its UN number is 1695.
