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Hexachloroacetone

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Hexachloroacetone
Hexachloroacetone
Names
Preferred IUPAC name 1,1,1,3,3,3-Hexachloropropan-2-one
Other names perchloroacetone
HCA
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.754 Edit this at Wikidata
EC Number
  • 204-129-5
KEGG
PubChem CID
RTECS number
  • UC2100000
UNII
UN number 2661
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9Key: DOJXGHGHTWFZHK-UHFFFAOYSA-N
  • InChI=1/C3Cl6O/c4-2(5,6)1(10)3(7,8)9Key: DOJXGHGHTWFZHK-UHFFFAOYAW
SMILES
  • ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl
Properties
Chemical formula C3Cl6O
Molar mass 264.75 g/mol
Density 1.7434 g/cm
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Reactions and uses

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

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:

(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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