Skip to content
aldrin

Structure via PubChem · Public domain (PubChem)

EntityQ409054· pop 30· linked from 268 articles

Also known as HHDN, 1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-endo-1,4-exo-5,8-dimethanonaphthalene, hexachlorohexahydro-endo-exo-dimethanonaphthalene

Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides (a term f

Chemical data

Formula
C12H8Cl6
Molecular weight
364.9 g/mol
IUPAC name
(1S,2S,3S,6R,7R,8R)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene
SMILES
C1[C@@H]2C=C[C@H]1[C@H]3[C@@H]2[C@]4(C(=C([C@@]3(C4(Cl)Cl)Cl)Cl)Cl)Cl
InChIKey
QBYJBZPUGVGKQQ-SJJAEHHWSA-N
XLogP
4.5
Polar surface area
0 Ų
H-bond donors
0
H-bond acceptors
0
Formal charge
0

via PubChem

Research

1,767 papers

via PubMed

Wikidata facts

Mass
361.875716336
Show 14 more facts
chemical formula
C₁₂H₈Cl₆
NIOSH Pocket Guide ID
0016
density
1.60
immediately dangerous to life or health
25
melting point
219
vapor pressure
0.00008
solubility
0.003
time-weighted average exposure limit
0.01
median lethal dose (LD50)
44
minimal lethal dose
5.8
short-term exposure limit
0.03
Commons category
Aldrin
isomeric SMILES
C1[C@@H]2C=C[C@H]1[C@H]3[C@@H]2[C@]4(C(=C([C@@]3(C4(Cl)Cl)Cl)Cl)Cl)Cl
canonical SMILES
ClC1=C(Cl)C2(Cl)C3C4C=CC(C4)C3C1(Cl)C2(Cl)Cl
Sources (7)

via Wikidata · CC0

~11 min read

Article

14 sections
Contents
  • Structure and Reactivity
  • Synthesis
  • Available forms
  • Mechanism of action
  • Neurotoxicity
  • Metabolism
  • Efficacy and side effects
  • Efficacy
  • Adverse effects
  • Toxicity
  • Effects on animals
  • Environmental impact and regulation
  • Safety and environmental aspects
  • References

Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. 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.

== Structure and Reactivity == Pure aldrin takes form as a white crystalline powder. Though it is not soluble in water (0.003% solubility), aldrin dissolves very well in organic solvents, such as ketones and paraffins. Aldrin decays very slowly once released into the environment. Though it is rapidly converted to dieldrin by plants and bacteria, dieldrin maintains the same toxic effects and slow decay of aldrin. Aldrin is easily transported through the air by dust particles. Aldrin does not react with mild acids or bases and is stable in an environment with a pH between 4 and 8. It is highly flammable when exposed to temperatures above 200 °C In the presence of oxidizing agents aldrin reacts with concentrated acids and phenols.

Gallery (3)

Connections

Categories