Aldrin

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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 InfoCard 100.005.652
EC Number 206-215-8
KEGG
PubChem {{{value}}}
RTECS number IO2100000
UNII
UN number 2762, 2761
SMILES {{{value}}}
Properties
C12H8Cl6
Molar mass 364.90 g·mol−1
Appearance colorless solid
Density 1.60 g/mL[1]
Melting point 104 °C (219 °F; 377 K)
slightly soluble (0.003%)[1]
Vapor pressure 7.5 × 10−5 mmHg @ 20 °C
Hazards
Main hazards potential occupational carcinogen[1]
NFPA 704

NFPA 704.svg

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).
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Infobox references

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[change | change source]

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[change | change source]

  1. 1.0 1.1 1.2 1.3 1.4 1.5 "NIOSH Pocket Guide to Chemical Hazards #0016". National Institute for Occupational Safety and Health (NIOSH).
  2. Jubb, A. H. (1975). Basic Organic Chemistry, Part 5 Industrial products. London: Wiley. ISBN 0-471-85014-4.