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| Names | |
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Preferred IUPAC name
(1r,2r,3r,4r,5r,6r)-1,2,3,4,5,6-Hexachlorocyclohexane | |
| Other names
β-HCH
β-Benzenehexachloride β-BHC | |
| Identifiers | |
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3D model (JSmol)
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| 1907338 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.703 |
| EC Number |
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| KEGG | |
| UNII | |
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CompTox Dashboard (EPA)
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| Properties | |
| C6H6Cl6 | |
| Molar mass | 290.83 g/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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β-Hexachlorocyclohexane (β-HCH) is an organochloride which is one of the isomers of hexachlorocyclohexane (HCH). It is a byproduct of the production of the insecticide lindane (γ-HCH). It is typically constitutes 5–14% of technical-grade lindane, though it has not been produced or used in the United States since 1985. As of 2009, the Stockholm Convention on Persistent Organic Pollutants classified α-hexachlorocyclohexane and β-HCH as persistent organic pollutants (POPs), due to the chemical's ability to persist in the environment, bioaccumulative, biomagnifying, and long-range transport capacity.
This pesticide was widely used during the 1960s and 1970s, particularly on cotton plants. Although banned as a pesticide more than 30 years ago, traces of beta-HCH can still be found in water and soil. Animal studies show that organochlorine pesticides, including beta-HCH, are neurotoxic, cause oxidative stress, and damage the brain's dopaminergic system. Human studies show that exposure to beta-HCH is linked to Parkinson's and Alzheimer's disease. β-HCH was present in elevated levels in some patients as recently as 2009. It was manufactured by exhausting chlorination of benzene and for this reason was called erroneously β-BHC. This synonym still persists.
In March 2005, the Italian National Monitoring System on Chemical Residuals in Food of Animal Origin detected levels of the pesticide β-HCH that were 20 times higher than the legal limit of 0.003 mg/kg in bulk milk from a dairy farm in the Sacco River valley. β-HCH, a lindane isomer and possible human carcinogen, was subsequently found in milk from several neighboring farms. A study was therefore undertaken to evaluate the extent and risk factors for contamination.