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Dieldrin



Dieldrin
IUPAC name 1,2,3,4,10,10-Hexachloro-6,7-epoxy-
1,4,4a,5,6,7,8,8a-octahydro-endo,exo-
1,4:5,8-dimethanonaphthalene
Other names Dieldrin
Identifiers
CAS number 60-57-1
SMILES ClC1(Cl)C2(Cl)C(C5C3C
(C4C5)O3)C4C(Cl)1C(Cl)=C2Cl
Properties
Molecular formula C12H8Cl6O
Molar mass 380.91 g/mol
Density 1.75 g/cm³
Melting point

176-177 °C

Boiling point

385 °C

Hazards
MSDS External MSDS
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Dieldrin is a chlorinated hydrocarbon originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. The molecule has a ring structure based on naphthalene.

Additional recommended knowledge

Dieldrin is closely related to aldrin which itself breaks down to form dieldrin. Aldrin is not toxic to insects, it is oxidised in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.

Originally developed in the 1940s as an alternative to DDT, dieldrin proved to be a highly effective insecticide and was very widely used during the 1950s to early 1970s. Endrin is a stereoisomer of dieldrin.

However, it is an extremely persistent organic pollutant, it does not easily break down. Furthermore it tends to accumulate as it is passed along the food chain. Long-term exposure has proven toxic to a very wide range of animals including humans, far greater than to the original insect targets. For this reason it is now banned in most of the world.

See also

References

    • S. Kegley, B. Hill, S. Orme, PAN Pesticide Database, Pesticide Action Network, North America (San Francisco, CA. 2007), http://www.pesticideinfo.org
     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dieldrin". A list of authors is available in Wikipedia.
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