Chloroacetone
Chemical compound
From Wikipedia, the free encyclopedia
Chloroacetone is a liquid, a chemical compound with the formula CH3COCH2Cl. Regulated for its potential as a tear gas, it is primarily a chemical intermediate in commerce.
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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 UN 1695 | |
| Identifiers | |
3D model (JSmol) |
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| 605369 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.056 |
| 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 |
| −50.9·10−6 cm3/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).
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Properties
Synthesis
Applications
Chloroacetone is primarily an intermediate in chemical manufacture. In the early 2000s, it was used to make dye couplers for colour film photography.[2] In the pharmaceutical industry, it is a precursor to phenoxyacetone.[6]
It is also used in the Feist-Benary synthesis of furans:[7]
Purification
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 regulations
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.