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]
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| 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: | |
  
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| 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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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
editThe 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
edit- ^ a b c Isobenzan, International Programme on Chemical Safety
- ^ Isobenzan at Sigma-Aldrich (dead link 3 March 2024)
- ^ 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities (PDF) (Report) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.
- ^ a b US3000907A, Hans, Feichtinger; Hans, Tummes & Siegfried, Puschhof, "Chlorinated 4,5,6,7,10,10-hexachloro-4,7-endomethylene - 4,7,8,9 - tetrahydrophthalane insecticides", issued 1961-09-19
- ^ Riemschneider, R.; Gallert, H.; Andres, P. (1961). "Zur Chemie von Polyhalocyclopentadienen, 22. Mitt.: Über die Herstellung von 1,4,5,6,7,7-Hexachlorbicyclo[2.2.1]hepten-(5)-bishydroxymethylen-(2,3)". Monatshefte für Chemie (in German). 92 (5): 1075–1079. doi:10.1007/BF00924776.
- ^ DE1020346B, Feichtinger, Dr Hans; Tummes, Dr Hans & Puschhof, Siegfried, "Insecticides and processes for their manufacture", issued 1957-12-05
- ^ Feichtinger, H.; Linden, H. W. (1965). "Telodrin, its synthesis and derivatives". Chemistry & Industry. 47: 1938–1940. PMID 5846097.
- ^ Feichtinger, H.; Linden, H.-W.: Friedel-Crafts-Reaktionen 1-substituierter 4.5.6.7.10.10-Hexachlor-4.7-methylen-4.7.8.9-tetrahydro-phthalane in Chem. Ber. 97 (1964) 2779–2784, doi:10.1002/cber.19640971009.
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