Beta-Hexachlorocyclohexane

β-hexachlorocyclohexane
IUPAC name β-1,2,3,4,5,6-hexachlorocyclohexane
Other names β-HCH β-Benzenehexachloride β-BHC
Identifiers
CAS number	319-85-7 Y
ChemSpider	10468512 Y
ChEBI	CHEBI:28428 Y
ChEMBL	CHEMBL389022 Y
Jmol-3D images	{{#if:Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl|Image 1
SMILES Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl
InChI InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6- Y Key: JLYXXMFPNIAWKQ-CDRYSYESSA-N Y InChI=1/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6- Key: JLYXXMFPNIAWKQ-CDRYSYESBR
Properties
Molecular formula	C6H6Cl6
Molar mass	290.83 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

β-hexachlorocyclohexane (β-HCH) is an organochloride which is one of the isomers of hexachlorocyclohexane (HCH).^[1] It is a byproduct of the production of the insecticide lindane (γ-HCH). It is typically constitutes 5-14% of technical grade lindane,^[2] though it has not been produced or used in the United States for more than 20 years, i.e. since 1985.^[1]

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.^[3] Beta-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 beta-BHC. This synnonym still persists.

In March 2005, the Italian National Monitoring System on Chemical Residuals in Food of Animal Origin detected levels of the pesticide beta-hexachlorocyclohexane (ß-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. ß-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. ^{[4] [5]}

See also

• α-Hexachlorocyclohexane

References

External links

• beta-Hexachlorocyclohexane (beta-HCH) Quickview – US EPA
• Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1α,2β,3α,4β,5α,6β)- – NIST