Names | |
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IUPAC name
1,3,4,5,6,7,8,8-Octachloro-1,3,3a,4,7,7a-hexahydro-4,7-methanoisobenzofuran
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Other names
Telodrin; 1,3,4,5,6,7,8,8-Octachloro-4,7-methylene-3a,4,7,7a-tetrahydro-isobenzofuran
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Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.005.497 |
EC Number |
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KEGG | |
PubChem
CID
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RTECS number |
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UNII | |
UN number | 2761 |
CompTox Dashboard (
EPA)
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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: | |
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) | |
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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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]
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]
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]