Isobenzan

Chemical compound From Wikipedia, the free encyclopedia

Isobenzan (telodrin) is a highly toxic organochloride insecticide. It was produced only in the period from 1958 to 1965 and its use has been since discontinued.[1] It is a persistent organic pollutant that can remain in soil for 2 to 7 years, and the biological half-life of isobenzan in human blood is estimated to be about 2.8 years.[1]

Quick facts Names, Identifiers ...
Isobenzan[1][2]
Names
IUPAC name
1,3,4,5,6,7,8,8-Octachloro-1,3,3a,4,7,7a-hexahydro-4,7-methanoisobenzofuran
Other names
Telodrin; 1,3,4,5,6,7,8,8-Octachloro-4,7-methylene-3a,4,7,7a-tetrahydro-isobenzofuran
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.497 Edit this at Wikidata
EC Number
  • 206-045-4
KEGG
RTECS number
  • PC1225000
UNII
UN number 2761
  • InChI=1S/C9H4Cl8O/c10-3-4(11)8(15)2-1(5(12)18-6(2)13)7(3,14)9(8,16)17/h1-2,5-6H
    Key: LRWHHSXTGZSMSN-UHFFFAOYSA-N
  • ClC1C2C3(Cl)C(Cl)=C(Cl)C(C3(Cl)Cl)(Cl)C2C(Cl)O1
Properties
C9H4Cl8O
Molar mass 411.73 g·mol−1
Appearance Whitish to light brown crystalline powder
Density 1.87 g/cm3
Melting point 121.3 °C (250.3 °F; 394.4 K)
Practically insoluble
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H300, H310, H320, H361, H370, H372, H410
P201, P202, P260, P262, P264, P270, P273, P280, P281, P301+P310, P302+P350, P305+P351+P338, P307+P311, P308+P313, P310, P314, P321, P322, P330, P337+P313, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
0
0
Flash point Non-flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[3]

Production

The precursor 4,5,6,7,10,10-hexachloro-4,7-endomethylene-4,7,8,9-tetrahydrophthalane can be obtained in two synthetic routes. In a synthesis method report published in 1954, 1,4,5,6,7,7-hexachloro-2,3-bishydroxymethylbicyclo[2,2,1]hept-5-ene is obtained, which is then dehydrated to the precursor.[4] In 1961, a direct preparation of the precursor via a Diels-Alder reaction with hexachlorocyclopentadiene and 2,5-Dihydrofuran was found.[5] The target compound is then synthesized by photochlorination of the precursor.[6][4][7][8]

References

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