Chloroacetone

Source: Wikipedia, the free encyclopedia.
Chloroacetone
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 Edit this at Wikidata
EC Number
  • 201-161-1
RTECS number
  • UC0700000
UNII
  • InChI=1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3 checkY
    Key: BULLHNJGPPOUOX-UHFFFAOYSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)

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

Feist-Benary synthesis of furans.[6]

  • 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

References

  1. ^ "ICSC:NENG0760 International Chemical Safety Cards (WHO/IPCS/ILO) CDC/NIOSH". Center for Disease Control. 2006-10-11. Retrieved 2009-04-17.
  2. ^ a b Hathaway, Gloria J.; Proctor, Nick H. (2004). Proctor and Hughes' Chemical Hazards of the Workplace (5 ed.). Wiley-Interscience. pp. 143–144. . Retrieved 2009-04-16.
  3. ^ "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.
  4. ^ "CHLOROACETONE". International Programme on Chemical Safety. Retrieved 2008-06-06.
  5. .
  6. ^ Li, Jie-Jack; Corey, E. J. (2004). Name Reactions in Heterocyclic Chemistry. Wiley-Interscience. p. 160. . Retrieved 2009-04-16.
  7. .
  8. ^ Phys. Chem. Chem. Phys., 2000,2, 237-245

External links