Endosulfan

Title: Endosulfan
CAS Registry Number: 115-29-7
CAS Name: 6,7,8,9,10,10-Hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin 3-oxide
Additional Names: 1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dimethanol cyclic sulfite; 1,2,3,4,7,7-hexachlorobicyclo[2.2.1]-2-heptene-5,6-bisoxymethylene sulfite; chlorthiepin
Trademarks: Malix (Bayer CropSci.); Thiodan (Bayer CropSci.); Thionex (Makhteshim-Agan)
Molecular Formula: C9H6Cl6O3S
Molecular Weight: 406.93
Percent Composition: C 26.56%, H 1.49%, Cl 52.27%, O 11.80%, S 7.88%
Literature References: Prepd by reaction of hexachlorocyclopentadiene with cis-butene-1,4-diol to form the bicyclic dialcohol, followed by esterification and cyclization with SOCl2: Geering, Nelson, US 2983732 (1961 to Hooker). Configuration studies: Reimschneider, Wuscherpfenning, Z. Naturforsch. 17b, 585 (1962); Forman et al., J. Org. Chem. 30, 169 (1965). Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969). Review of toxicology and human exposure: Toxicological Profile for Endosulfan (PB2000-108023, 2000) 323 pp.
Properties: Commercial product brown crystals. mp 70-100° (pure mp 106°). Practically insol in water. Sol in most organic solvents. Stable toward dil mineral acids; hydrolyzed rapidly by alkalies. Commercial product is a mixture of a-isomer, mp 108-110°, and b-isomer, mp 208-210°. LD50 orally in male, female rats: 43, 18 mg/kg (Gaines).
Melting point: mp 70-100°; pure mp 106°; mp 108-110°; mp 208-210°
Toxicity data: LD50 orally in male, female rats: 43, 18 mg/kg (Gaines)
CAUTION: Potential symptoms of overexposure are skin irritation; nausea, confusion, agitation, flushing, dry mouth, tremors, convulsions, headache. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 126.
Use: Insecticide.
Endothall Endothelin Endralazine Endrin Enduracidin

Endosulfan
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 115-29-7 YesY
ChemSpider 21117730 YesY
UNII QY5Y9R7G0E YesY
KEGG C11090 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H6Cl6O3S
Molar mass 406.93 g mol−1
Density 1.745 g/cm³
Melting point 70 to 100 °C; 158 to 212 °F; 343 to 373 K
Solubility in water 0.33 mg/L
Hazards
EU classification Yes (T, Xi, N)
R-phrases R24/25 R36 R50/53
Main hazards T, Xi, N
NFPA 704
NFPA 704.svg
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Endosulfan is an off-patent organochlorine insecticide and acaricide that is being phased out globally. The two isomers, endo and exo, are known popularly as I and II. Endosulfan sulfate is a product of oxidation containing one extra O atom attached to the S atom. Endosulfan became a highly controversial agrichemical[1] due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. Because of its threats to human health and the environment, a global ban on the manufacture and use of endosulfan was negotiated under the Stockholm Convention in April 2011. The ban will take effect in mid-2012, with certain uses exempted for five additional years.[2] More than 80 countries,[3] including the European Union, Australia, New Zealand, several West African nations,[4] the United States,[5][6] Brazil,[7] and Canada[8] had already banned it or announced phase-outs by the time the Stockholm Convention ban was agreed upon. It is still used extensively in India, China, and few other countries. It is produced by Makhteshim Agan and several manufacturers in India and China.