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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
Other names Hexachlorophenol
Identifiers
CAS Number
3D model (JSmol)
Abbreviations HCP
ChemSpider
PubChem CID
RTECS number
  • SN1575000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6Cl6O/c7-1-3(13)2(8)5(10)6(11,12)4(1)9Key: SLKWROUNLHVIIQ-UHFFFAOYSA-N
SMILES
  • ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C(Cl)C1=O
  • O=C1C(=C(Cl)C(Cl)(Cl)C(=C1Cl)Cl)Cl
Properties
Chemical formula C6Cl6O
Molar mass 300.77 g·mol
Melting point 113 °C (235 °F; 386 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P280, P302+P352, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. 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 polychlorinated benzenes 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.

References

  1. "SAFETY DATA SHEET". ThermoFisher Scientific. 18 December 2020.
  2. S. Gali, C. Miravitlles and M. Font-Altaba "Hexachlorocyclohexa-2,5-dienone" Acta Crystallogr. 1975, volume B31, p. 2510-2512. doi:10.1107/S0567740875007935.
  3. François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3527306732.

See also

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