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β-hexachlorocyclohexane

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Also known as beta-benzene hexachloride, beta-BHC, beta-1,2,3,4,5,6-hexachlorocyclohexane, beta-lindane, beta-HCH, trans-1,2,3,4,5,6-hexachlorocyclohexane, (1alpha,2beta,3alpha,4beta,5alpha,6beta)-1,2,3,4,5,6-hexachlorocyclohexane

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 capaci

Wikidata facts

Mass
287.8601
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chemical formula
C₆H₆Cl₆
canonical SMILES
C1(C(C(C(C(C1Cl)Cl)Cl)Cl)Cl)Cl
isomeric SMILES
[C@@H]1([C@@H]([C@H]([C@@H]([C@H]([C@@H]1Cl)Cl)Cl)Cl)Cl)Cl
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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.

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