Isobenzan

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]

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
CAS Number	297-78-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82099
ChemSpider	8914
ECHA InfoCard	100.005.497
EC Number	206-045-4
KEGG	C18960 Y
PubChem CID	9271
RTECS number	PC1225000
UNII	8IAN133486
UN number	2761
CompTox Dashboard (EPA)	DTXSID3021306
InChI 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
SMILES ClC1C2C3(Cl)C(Cl)=C(Cl)C(C3(Cl)Cl)(Cl)C2C(Cl)O1
Properties
Chemical formula	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)
Solubility in water	Practically insoluble
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H320, H361, H370, H372, H410
Precautionary statements	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)	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). Y verify (what is YN ?) Infobox references

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]