Hexachlorocyclohexa-2,5-dien-1-one
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| 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  | |||
| 3D model (Jmol) | Interactive image Interactive image | ||
| ChemSpider | 62251 | ||
| PubChem | 69029 | ||
| RTECS number | SN1575000 | ||
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| Properties | |||
| C6Cl6O | |||
| Molar mass | 300.77 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 otherwise noted, data are 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. 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 phenolsulphonic acids and benzenesulphonic acids followed by removal of the sulphonic acid group. The hydrolysis of HCP gives chloranil.[2]
References
- ↑ S. Gali, C. Miravitlles and M. Font-Altaba "Hexachlorocyclohexa-2,5-dienone" Acta Crystallogr. 1975, volume B31, p. 2510-2512. doi:10.1107/S0567740875007935.
- ↑ François Muller and Liliane Caillard "Chlorophenols" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2011. doi:10.1002/14356007.a07_001.pub2