Hexachlorobenzene
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IUPAC name
Hexachlorobenzene
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| Other names
Perchlorobenzene; Benzene hexachloride; HCB; BHC
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3D model (Jmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.003.886 | ||
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PubChem CID
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| Properties | |||
| C6Cl6 | |||
| Molar mass | 284.80 g/mol | ||
| Density | 2.04 g/cm3 | ||
| Melting point | 231 °C (448 °F; 504 K) | ||
| Boiling point | 323 to 326 °C (613 to 619 °F; 596 to 599 K) | ||
| -147.5·10−6 cm3/mol | |||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
Hexachlorobenzene, or perchlorobenzene, is an organochloride with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the on persistent organic pollutants.
HCB is a white crystalline solid that has negligible solubility in water (0.00000002 M) and variable solubility in different organic solvents. It is most soluble in halogenated solvents like chloroform (approx 0.03 M) less soluble in esters and hydrocarbons (approx 0.020 M), and even less soluble in short chain alcohols (0.002-0.006 M). Its vapour pressure is 1.09×10−5 mmHg (1.45 mPa) at 20 °C. Its flash point is 242 °C and it sublimes at 322 °C.
Hexachlorobenzene is an animal carcinogen and is considered to be a probable human carcinogen. After its introduction as a fungicide in 1945, for crop seeds, this toxic chemical was found in all food types. Hexachlorobenzene was banned from use in the United States in 1966.
This material has been classified by the International Agency for Research on Cancer (IARC) as a Group 2B carcinogen (possibly carcinogenic to humans). Animal carcinogenicity data for hexachlorobenzene show increased incidences of liver, kidney (renal tubular tumours) and thyroid cancers. Chronic oral exposure in humans has been shown to give rise to a liver disease (porphyria cutanea tarda), skin lesions with discoloration, ulceration, photosensitivity, thyroid effects, bone effects and loss of hair. Neurological changes have been reported in rodents exposed to hexachlorobenzene. Hexachlorobenzene may cause embryolethality and teratogenic effects. Human and animal studies have demonstrated that hexachlorobenzene crosses the placenta to accumulate in foetal tissues and is transferred in breast milk.
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