Preferred IUPAC name
Acetonyl chloride, chloropropanone, 1-chloro-2-propanone, monochloroacetone, 1-chloro-2-ketopropane, 1-chloro-2-oxypropane
ECHA InfoCard 100.001.056
C 3 H 5 Cl O
g·mol 92.52 −1
Colorless liquid, oxidizes to amber
1.123 g/cm 3
−44.5 °C (−48.1 °F; 228.7 K)
119 °C (246 °F; 392 K)
10 g/100 mL at 20 °C
miscible with alcohol, ether, chloroform
-50.9·10 −6 cm 3/mol
35 °C (95 °F; 308 K)
610 °C (1,130 °F; 883 K)
3.4% - ?
Lethal dose or concentration (LD, LC):
100 mg/kg (rats, oral)
Except where otherwise noted, data are given for materials in their
(at 25 °C [77 °F], 100 kPa).
Chloroacetone is a chemical compound with the formula . At C H 3C OCH 2 Cl STP it is a colourless liquid with a pungent odour. On exposure to light, it turns to a dark yellow-amber colour.  It was used as a  tear gas in World War I.
Synthesis [ ]
Chloroacetone may be synthesized from the reaction between
chlorine and diketene, or by the chlorination of acetone.
Applications [ ]
Chloroacetone is used to make
dye couplers for colour photography, and is an intermediate in chemical manufacturing. It is also used in the  Feist-Benary synthesis of furans.
Reaction of phenoxide with chloroacetone gives phenoxyacetone, 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 KMnO 4 to form a diol (followed by separation with ether), which is removed on subsequent distillation.
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.
See also [ ]
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). (5 ed.). Wiley-Interscience. pp. 143–144. Proctor and Hughes' Chemical Hazards of the Workplace 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
Haber, Ludwig Fritz (1986). The Poisonous Cloud: Chemical Warfare in the First World War. Oxford University Press. ISBN . 0-19-858142-4
Li, Jie-Jack; Corey, E. J. (2004). . Wiley-Interscience. p. 160. Name Reactions in Heterocyclic Chemistry ISBN 978-0-471-30215-5 . Retrieved . 2009-04-16
Hurd, Charles D.; Perletz, Percy (1946). "Aryloxyacetones1". Journal of the American Chemical Society. 68 (1): 38–40. doi: 10.1021/ja01205a012. ISSN 0002-7863.
^ Phys. Chem. Chem. Phys., 2000,2, 237-245
External links [ ]