Hexachloroacetone

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Hexachloroacetone
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 Edit this at Wikidata
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 Â°C (28 Â°F; 271 K)
Boiling point 204 Â°C (399 Â°F; 477 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Reactions and uses

Hexachloroacetone functions equivalently to trichloroacetyl chloride, i.e. as a 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

Links

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