Aldrin

For other uses, see Aldrin (disambiguation).

Aldrin

Names
IUPAC names 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 Y
ChemSpider	10292747 Y
Jmol 3D model	Interactive image
KEGG	C07552 Y
UNII	OZE3CLY605 Y
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
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
Chemical formula	C12H8Cl6
Molar mass	364.90 g·mol−1
Appearance	colorless solid
Density	1.60 g/mm3
Melting point	104 °C (219 °F; 377 K)
Solubility in water	slightly soluble (0.003%)
Vapor pressure	7.5 × 10−5 mmHg @ 20 °C
Vapor pressure	{{{value}}}
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

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 (a term for pesticides derived from Hexachlorocyclopentadiene) became notorious as persistent organic pollutants.

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

Similarly, an isomer of aldrin, known as isodrin, is produced by reaction of hexachloronobornadiene with cyclopentadiene.

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.

Safety and environmental aspects

Aldrin has rat LD₅₀ of 39 to 60 mg/kg (oral in rats). For fish however, it is extremely toxic, with an LC50 of 0.006 – 0.01 for trout and bluegill.

In the US, aldrin is considered a potential occupational carcinogen by the Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health; these agencies have set an occupational exposure limit for dermal exposures at 0.25 mg/m³ over an eight-hour time-weighted average. Further, an IDLH limit has been set at 25 mg/m³, based on acute toxicity data in humans to which subjects reacted with convulsions within 20 minutes of exposure.