Hexachloroacetone

Hexachloroacetone is an organic compound with the formula (Cl3C)2CO. It is also called hexachloropropanone or perchloroacetone. Numbers indicating the position of the chlorine-atoms are generally omitted as all the possible positions are substituted with chlorine. It is a colorless liquid, slightly soluble in water.

Hexachloroacetone
Hexachloroacetone
Names
Preferred IUPAC name
1,1,1,3,3,3-Hexachloropropan-2-one
Other names
perchloroacetone
HCA
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.754
EC Number
  • 204-129-5
KEGG
RTECS number
  • UC2100000
UNII
UN number 2661
  • InChI=1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 checkY
    Key: DOJXGHGHTWFZHK-UHFFFAOYSA-N checkY
  • InChI=1/C3Cl6O/c4-2(5,6)1(10)3(7,8)9
    Key: DOJXGHGHTWFZHK-UHFFFAOYAW
  • ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl
Properties
C3Cl6O
Molar mass 264.75 g/mol
Density 1.7434 g/cm3[1]
Melting point −2 °C (28 °F; 271 K)
Boiling point 204 °C (399 °F; 477 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reactions and uses

Hexachloroacetone functions equivalently to trichloroacetyl chloride, i.e. as an trichloroacetylating agent.[2]

The main use of hexachloroacetone is as a pesticide. For the use of hexachloroacetone in the preparation of a novel insect repellent see Perkow reaction. The industrial route to hexafluoroacetone involves treatment of hexachloroacetone with HF:[3]

(CCl3)2CO + 6 HF → (CF3)2CO + 6 HCl

See also

References
  1. CRC Handbook of Chemistry and Physics, Internet Version, CRC Press (2005)
  2. Bernard Sukornick (1960). "α,α,α-Trichloroacetanilide". Organic Syntheses. 40: 103. doi:10.15227/orgsyn.040.0103.
  3. Günter Siegemund; Werner Schwertfeger; Andrew Feiring; Bruce Smart; Fred Behr; Herward Vogel; Blaine McKusick (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN 3-527-30673-0.


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