Chloroacetone

Chemical compound From Wikipedia, the free encyclopedia

Chloroacetone

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 gas in World War I.[5]

Quick Facts Names, Identifiers ...
Chloroacetone
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Names
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)
605369
ChEBI
ChemSpider
ECHA InfoCard 100.001.056
EC Number
  • 201-161-1
RTECS number
  • UC0700000
UNII
  • InChI=1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3 Y
    Key: BULLHNJGPPOUOX-UHFFFAOYSA-N Y
  • Key: BULLHNJGPPOUOX-UHFFFAOYAY
  • ClCC(=O)C
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):
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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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.[2] It is also used in the Feist-Benary synthesis of furans.[6]

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  • 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 US Department of Transportation. Stabilized chloroacetone is in hazard class 6.1 (Poison Inhalation Hazard). Its UN number is 1695.

See also

References

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