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Aldrin
Aldrin.svg
Aldrin-from-xtal-3D-balls.png
IUPAC name 1,2,3,4,10,10-Hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene
Other names HHDN
octalene
Identifiers
CAS number 309-00-2
PubChem 2087
KEGG C07552
ChEBI CHEBI:2564
RTECS number IO2100000
SMILES ClC4(Cl)[C@@]2(Cl)C(/Cl)=C(/Cl)[C@]4(Cl)[C@@H]3[C@@H]\1C[C@@H](/C=C/1)[C@H]23
Properties
Molecular formula C12H8Cl6
Molar mass 364.91 g mol-1
Appearance colorless solid
Density 1.60 g/mL
Melting point

104 °C, 377 K, 219 °F

Solubility in water slightly soluble (0.003%)
Vapor pressure 7.5 × 10−5 mmHg @ 20 °C
Hazards
Main hazards potential occupational carcinogen
NFPA 704

NFPA 704.svg

0
4
0
 
U.S. Permissible
exposure limit (PEL)
TWA 0.25 mg/m3 [skin]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Aldrin is an insecticide, which was used against termites, locusts and the larvae of Click beetles. Most plants and animals convert it to Dieldrin. It is listed in the Stockholm Convention on Persistent Organic Pollutants, its production, use and trade are banned since 2004. Aldrin is a neurotoxin. People inhaling it can develop headaches, but also seizures. In humans, Aldrin is converted to dieldrin in the liver. The change will mean that it can leave the body again. The problem is that the change is slow, and the half-life is about a year. Aldrin may be a teratogen, and it probably causes cancer.

Production

Aldrin is produced by combining hexachlorocyclopentadiene with norbornadiene in a Diels-Alder reaction to give the adduct.

AldrinSynthesis
Synthesis of Aldrin via a Diels-Alder reaction

Aldrin is named after the German chemist Kurt Alder, one of the coinventors of this kind of reaction. An estimated 270 million kilograms of aldrin and related cyclodiene pesticides were produced between 1946 and 1976.

In soil, on plant surfaces, or in the digestive tracts of insects, aldrin oxidizes to the epoxide, dieldrin. Dieldrin is more strongly insecticidal than aldrin.

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