Kepone

Kepone
Names


IUPAC name decachloropentacyclo[5.3.0.0^2.6.0^3.9.0^4.8]decan-5-one
Other names Chlordecone Clordecone Merex CAS name: 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalen-2-one
Identifiers
CAS Number	143-50-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16548^N
ChemSpider	293^Y
ECHA InfoCard	100.005.093
EC Number	205-601-3
KEGG	C01792^Y
PubChem CID	299
UNII	RG5XJ88UDF^N
InChI InChI=1S/C10Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20^Y Key: LHHGDZSESBACKH-UHFFFAOYSA-N^Y InChI=1/C10Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20 Key: LHHGDZSESBACKH-UHFFFAOYAM
SMILES ClC54C(=O)C1(Cl)C2(Cl)C5(Cl)C3(Cl)C4(Cl)C1(Cl)C2(Cl)C3(Cl)Cl
Properties
Chemical formula	C₁₀Cl₁₀O
Molar mass	490.633 g/mol
Appearance	tan to white crystalline solid
Odor	odorless
Density	1.6 g/cm³
Melting point	349 °C (660 °F; 622 K) (decomposes)
Solubility in water	0.27 g/100 mL
Solubility	soluble in acetone, ketone, acetic acid slightly soluble in benzene, hexane
log P	5.41
Vapor pressure	3.10⁻⁷ kPa
Thermochemistry
Std molar entropy (S^o₂₉₈)	764 J/K mol
Std enthalpy of formation (Δ_fH^o₂₉₈)	-225.9 kJ/mol
Hazards
Main hazards	carcinogen
Flash point	Non-flammable
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	95 mg/kg (rat, oral)
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	Ca TWA 0.001 mg/m³
IDLH (Immediate danger)	N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Kepone, also known as chlordecone, is an organochlorine compound and a colourless solid. This compound is a controversial insecticide related to Mirex and DDT. Its use was so disastrous that it is now prohibited in the western world, but only after many millions of kilograms had been produced. Kepone is a known persistent organic pollutants (POP), classified among the "dirty dozen" and banned globally by the as of 2011.

The LC50 (LC = lethal concentration) is 35 μg/ L for Etroplus maculatus, 0.022–0.095 mg/kg for blue gill and trout. Kepone bioaccumulates in animals by factors up to a million-fold. Workers with repeated exposure suffer severe convulsions resulting from degradation of the synaptic junctions.

Kepone has been found to act as an agonist of the GPER (GPR30).

In the US, kepone was produced by Allied Signal Company and LifeSciences Product Company in Hopewell, Virginia. The improper handling and dumping of the substance into the nearby James River (U.S.) in the 1960s and 1970s drew national attention to its toxic effects on humans and wildlife. The product is similar to DDT and is a degradation product of Mirex. The history of Kepone incidents are reviewed in Who's Poisoning America?: Corporate Polluters and Their Victims in the Chemical Age (1982). In 2009, Kepone was included in the , which bans its production and use worldwide.

Due to the pollution risks, many businesses and restaurants along the river suffered economic losses. In 1975 Governor Mills Godwin Jr. shut down the James River to fishing for 100 miles, from Richmond to the Chesapeake Bay. This ban remained in effect for 13 years, until efforts to clean up the river began to get results.

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