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

Aldrin
Aldrin
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
RTECS number
  • IO2100000
UNII
UN number 2762, 2761
  • 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 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
Occupational safety and health (OHS/OSH):
Main hazards
 potential occupational carcinogen[1]
GHS labelling:
Template:GHS06Template:GHS08Template:GHS09
Danger
H300, H301, H310, H311, H351, H372, H410
P201, P202, P260, P262, P264, P270, P273, P280, P281, P301+P310, P302+P350, P302+P352, P308+P313, P310, P312, P314, P321, P322, P330, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
0
0
Flash point 66 °C (151 °F; 339 K)
Lethal dose or concentration (LD, LC):
50 mg/kg (rabbit, oral)
33 mg/kg (guinea pig, oral)
39 mg/kg (rat, oral)
44 mg/kg (mouse, oral)[2]
5.8 mg/m3 (rat, 4 hr)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.25 mg/m3 [skin][1]
REL (Recommended)
 Ca TWA 0.25 mg/m3 [skin][1]
IDLH (Immediate danger)
 25 mg/m3[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

Aldrin is produced by combining hexachlorocyclopentadiene with norbornadiene in a Diels-Alder reaction to give the adduct.[3]

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

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 NIOSH Pocket Guide to Chemical Hazards. "#0016". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ 2.0 2.1 "Aldrin". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
  3. ↑ Jubb, A. H. (1975). Basic Organic Chemistry, Part 5 Industrial products. London: Wiley. ISBN 0-471-85014-4.

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