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Hexachlorocyclohexa-2,5-dien-1-one

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Hexachlorocyclohexa-2,5-dien-1-one
Structural formula of hexachlorocyclohexa-2,5-dien-1-one
Structural formula of hexachlorocyclohexa-2,5-dien-1-one
Hexachlorophenol molecule
Names
Preferred IUPAC name
2,3,4,4,5,6-Hexachlorocyclohexa-2,5-dien-1-one
Systematic IUPAC name
Hexachlorocyclohexa-2,5-dien-1-one
Other names
Hexachlorophenol
Identifiers
3D model (JSmol)
ChemSpider
RTECS number
  • SN1575000
  • InChI=1S/C6Cl6O/c7-1-3(13)2(8)5(10)6(11,12)4(1)9
    Key: SLKWROUNLHVIIQ-UHFFFAOYSA-N
  • ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C(Cl)C1=O
  • O=C1C(=C(Cl)C(Cl)(Cl)C(=C1Cl)Cl)Cl
Properties
C6Cl6O
Molar mass 300.77 g·mol−1
Melting point 113 °C (235 °F; 386 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hexachlorocyclohexa-2,5-dien-1-one, sometimes informally called hexachlorophenol (HCP) is an organochlorine compound. It can be prepared from phenol. Despite the informal name, the compound is not a phenol but is a ketone.[1] The informal name is derived from its method of preparation which includes phenol as a reagent.

Preparation

HCP is normally produced by chlorination of phenol by chlorine in the presence of metal chloride catalyst, such as ferric chloride. It can also be produced by alkaline hydrolysis of polychlorinatedbenzenes at high temperature and pressure, by conversion of diazonium salts of chlorinated anilines, or by chlorination of phenolsulfonic acids and benzenesulfonic acids followed by removal of the sulfonic acid group. The hydrolysis of HCP gives chloranil.[2]

References

  1. ^ S. Gali, C. Miravitlles and M. Font-Altaba "Hexachlorocyclohexa-2,5-dienone" Acta Crystallogr. 1975, volume B31, p. 2510-2512. doi:10.1107/S0567740875007935.
  2. ^ "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2011. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3527306732. {{cite encyclopedia}}: Cite uses deprecated parameter |authors= (help)

See also

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