Aldrin

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.

Aldrin
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
InChI InChI=1/C12H8Cl6/c13-8-9(14)11(16)7-5-2-1-4(3-5)6(7)10(8,15)12(11,17)18/h1-2,4-7H,3H2/t4-,5+,6+,7-,10+,11-
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	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)

Production

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

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.