Hexachlorocyclohexa-2,5-dien-1-one
Chemical compound
From Wikipedia, the free encyclopedia
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 may be derived from its method of preparation, which includes phenol as a reagent. It is a white solid with herbicidal properties.
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| Names | |||
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| Preferred IUPAC name
2,3,4,4,5,6-Hexachlorocyclohexa-2,5-dien-1-one | |||
| Other names
Hexachlorophenol | |||
| Identifiers | |||
3D model (JSmol) |
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| Abbreviations | HCP | ||
| ChemSpider | |||
PubChem CID |
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| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| C6Cl6O | |||
| Molar mass | 300.77 g·mol−1 | ||
| Melting point | 113 °C (235 °F; 386 K) | ||
| Structure[1] | |||
| Tetragonal | |||
| I41/a | |||
| 4/m | |||
a = 21.796 Å, c = 8.568 Å | |||
Lattice volume (V) |
4070.36 Å3 | ||
Formula units (Z) |
16 | ||
| Hazards[2] | |||
| GHS labelling: | |||
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| Warning | |||
| H315, H319, H335 | |||
| P261, P280, P302+P352, P305+P351+P338 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and reactions
HCP is normally produced by chlorination of phenol by chlorine in aqueous acetic acid.[3]
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.[citation needed]