Chlordecone

Title: Chlordecone
CAS Registry Number: 143-50-0
CAS Name: 1,1a,3,3a,4,5,5,5a,5b,6-Decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalen-2-one
Additional Names: GC-1189
Trademarks: Kepone (Allied Chemical)
Molecular Formula: C10Cl10O
Molecular Weight: 490.64
Percent Composition: C 24.48%, Cl 72.26%, O 3.26%
Literature References: Prepn: Gilbert, Giolito, US 2616825 and US 2616928 (1952 to Allied Chem.); reissued as US RE 24435 (1958). Structure: McBee et al., J. Am. Chem. Soc. 78, 1511 (1956). Review: Ungnade, McBee, Chem. Rev. 58, 249-320 (1958). Toxicity data: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969). Occupational exposure: Chem. Eng. News 54, 19 (Feb. 2, 1976). Comparative toxicity in man and animals: P. S. Guzelian, Annu. Rev. Pharmacol. Toxicol. 22, 89-113 (1982). Review of toxicology and human exposure: Toxicological Profile for Mirex and Chlordecone (PB95-264354, 1995) 362 pp.
Properties: Crystals, dec 350°. Slightly sol in water and hydrocarbon solvents. Sol in alcohols, ketones, acetic acid. LD50 orally in rats: 125 mg/kg (Gaines).
Toxicity data: LD50 orally in rats: 125 mg/kg (Gaines)
CAUTION: Potential symptoms of overexposure are headache, nervousness, tremor; liver and kidney damage; visual disturbances; ataxia, chest pain, skin erythema; testicular atrophy, low sperm count. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 184. See also Patty's Industrial Hygiene and Toxicology vol. 2B, G. D. Clayton, F. E. Clayton, Eds. (John Wiley & Sons, New York, 4th ed., 1994) 1504-1506, 1545-1550. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-158.
Use: Formerly as insecticide, fungicide.
Chlordimeform Chlorendic Anhydride Chlorfenac Chlorfenapyr Chlorfenethol

Kepone
Chlordecone.png
Chlordecone Kepone 3D.png
Identifiers
CAS number 143-50-0 YesY
PubChem 299
ChemSpider 293 YesY
UNII RG5XJ88UDF N
EC number 205-601-3
KEGG C01792 YesY
ChEBI CHEBI:16548 N
ChEMBL CHEMBL462576 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10Cl10O
Molar mass 490.64 g mol−1
Appearance tan to white crystalline solid
Odor odorless
Density 1.6 g/cm3
Melting point 349 °C; 660 °F; 622 K (decomp)
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 So298
764 J/K mol
Std enthalpy of
formation ΔfHo298
-225.9 kJ/mol
Hazards
Flash point Non-flammable
LD50 95 mg/kg (rat, oral)
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Kepone, also known as chlordecone, is an organochlorine compound. It is 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.[2]