Chloroacetone
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
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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
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3.4% - ?[1] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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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Chloroacetone is a
tear gas in World War I.[5]
Synthesis
Chloroacetone may be synthesized from the reaction between chlorine and diketene, or by the chlorination of acetone.
Applications
Chloroacetone is used to make
- Reaction of phenoxide with chloroacetone gives phenoxyacetone,[7] which is used to make a wide variety of different pharmaceuticals. A catalytic amount of potassium iodide is also necessary to facilitate a Finkelstein reaction.
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
hazard class 6.1 (Poison Inhalation Hazard). Its UN number
is 1695.
See also
- Bromoacetone
- Dichloroacetone
- Fluoroacetone
- Hexachloroacetone
- Use of poison gas in World War I
References
- ^ "ICSC:NENG0760 International Chemical Safety Cards (WHO/IPCS/ILO) CDC/NIOSH". Center for Disease Control. 2006-10-11. Retrieved 2009-04-17.
- ^ a b
Hathaway, Gloria J.; Proctor, Nick H. (2004). Proctor and Hughes' Chemical Hazards of the Workplace (5 ed.). Wiley-Interscience. pp. 143–144. ISBN 978-0-471-26883-3. Retrieved 2009-04-16.
- ^ "Occupational Safety and Health Guideline for Chloroacetone". U.S. Department of Labor - Occupational Safety & Health Administration. Archived from the original on 2013-05-03. Retrieved 2008-06-06.
- ^ "CHLOROACETONE". International Programme on Chemical Safety. Retrieved 2008-06-06.
- ISBN 0-19-858142-4.
- ^
Li, Jie-Jack; Corey, E. J. (2004). Name Reactions in Heterocyclic Chemistry. Wiley-Interscience. p. 160. ISBN 978-0-471-30215-5. Retrieved 2009-04-16.
- ISSN 0002-7863.
- ^ Phys. Chem. Chem. Phys., 2000,2, 237-245