Aldrin

chemical compound

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
Names
IUPAC name
1,2,3,4,10,10-Hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene
Other names
HHDN[1]
octalene[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.005.652
EC Number
  • 206-215-8
KEGG
PubChem CID
RTECS number
  • IO2100000
UNII
UN number2762, 2761
CompTox Dashboard (EPA)
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
C12H8Cl6
Molar mass364.90 g·mol−1
Appearancecolorless solid
Density1.60 g/mL[1]
Melting point 104 °C (219 °F; 377 K)
slightly soluble (0.003%)[1]
Vapor pressure7.5 × 10−5 mmHg @ 20 °C
Hazards
Main hazardspotential occupational carcinogen[1]
NFPA 704

0
4
0
 
U.S. Permissible
exposure limit (PEL)
TWA 0.25 mg/m3 [skin][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

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. Dieldrin is more strongly insecticidal than aldrin.

References