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
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
599-52-0 YesY
ChemSpider 62251 YesY
Jmol-3D images Image
Image
PubChem 69029
RTECS number SN1575000
Properties
C6Cl6O
Molar mass 300.78 g·mol−1
Melting point 113 °C (235 °F; 386 K)
Hazards
R-phrases R22,R36,R38,R40,R50,R53
S-phrases (S2),S36,S37,S60,S61
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Hexachlorocyclohexa-2,5-dien-1-one, sometimes informally called hexachlorophenol (HCP) is an organochlorine compound which 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[edit]

HCP is normally produced by electrophilic chlorination of phenol by chlorine gas in the presence of metal chloride catalyst, such as ferric chloride. It can also be produced by alkaline hydrolysis of chlorobenzenes at high temperature and pressure, by conversion of diazonium salts of chlorinated anilines, or by chlorination of phenolsulphonic acids and benzenesulphonic acids followed by removal of the sulphonic acid group.

References[edit]

  1. ^ S. Gali, C. Miravitlles and M. Font-Altaba "Hexachlorocyclohexa-2,5-dienone" Acta Cryst. 1975, volume B31, p. 2510-2512. doi:10.1107/S0567740875007935.

See also[edit]