Aldrin

Aldrin
IUPAC name 1,2,3,4,10,10-Hexachloro- 1,4,4a,5,8,8a-hexahydro- 1,4:5,8-dimethanonaphthalene
Identifiers
CAS number	309-00-2 Y
ChemSpider	10292747 Y
UNII	OZE3CLY605 Y
KEGG	C07552 Y
Jmol-3D images	Image 1
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=1S/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- Y Key: QBYJBZPUGVGKQQ-SJJAEHHWSA-N Y 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- Key: QBYJBZPUGVGKQQ-SJJAEHHWBI
Properties
Molecular formula	C12H8Cl6
Molar mass	364.91 g mol−1
Melting point	104 °C
Vapor pressure	7.5 × 10−5 mmHg @ 20 °C
Hazards
NFPA 704	0 2 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aldrin is an organochlorine insecticide that was widely used until the 1970s, when it was banned in most countries. It is a colourless solid. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.^[1]

Production

Aldrin is produced by combining hexachlorocyclopentadiene with norbornadiene in a Diels-Alder reaction to give the adduct.^[2]

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, which is more strongly insecticidal

Environmental impact and regulation

Like related polychlorinated pesticides, aldrin is highly lipophilic. Its solubility in water is only 0.027 mg/L, which exacerbates its persistence in the environment. It was banned by the Stockholm Convention on Persistent Organic Pollutants. In the U.S., aldrin was cancelled in 1974. The substance is banned from use for plant protection by the EU. ^[3]

Safety and environmental aspects

Aldrin has rat LD₅₀ of 39 to 60 mg/kg (oral in rats).

References