Structure via PubChem · Public domain (PubChem)
dieldrin
Sign in to saveAlso known as (1aR,2R,2aS,3S,6R,6aR,7S,7aS)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxirene, HEOD, (1aalpha,2beta,2aalpha,3beta,6beta,6aalpha,7beta,7aalpha)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxirene, 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo,exo-5,8-dimethanonaphthalene, 2,7:3,6-dimethanonaphth[2,3-b]oxirene, 3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-, (1aalpha,2beta,2aalpha,3beta,6beta,6aalpha,7beta,7aalpha)-, 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo-exo-5,8-dimethanonaphthalene, (1R,4S,4aS,5R,6R,7S,8S,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene
Dieldrin is an organochlorine compound originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels–Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.
Chemical data
- Formula
- C12H8Cl6O
- Molecular weight
- 380.9 g/mol
- IUPAC name
- (1R,2S,3S,6R,7R,8S,9S,11R)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
- SMILES
- C1[C@@H]2[C@H]3[C@@H]([C@H]1[C@H]4[C@@H]2O4)[C@]5(C(=C([C@@]3(C5(Cl)Cl)Cl)Cl)Cl)Cl
- InChIKey
- DFBKLUNHFCTMDC-PICURKEMSA-N
- XLogP
- 3.7
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
3,985 papers- Mode of action of dieldrin-induced liver tumors: application to human risk assessment.Critical reviews in toxicology · 2024
- Bioremediation of the organochlorine pesticides, dieldrin and endrin, and their occurrence in the environment.Applied microbiology and biotechnology · 2009
- Monograph: reassessment of human cancer risk of aldrin/dieldrin.Toxicology letters · 1999
- Hazard identification of the potential for dieldrin carcinogenicity to humans.Environmental research · 2014
- Dieldrin toxidosis: rat reproduction.American journal of veterinary research · 1970
via PubMed
Wikidata facts
- Mass
- 377.87063095599996
Show 11 more facts
- chemical formula
- C₁₂H₈Cl₆O
- density
- 1.75
- immediately dangerous to life or health
- 50
- melting point
- 349
- NIOSH Pocket Guide ID
- 0206
- solubility
- 0.02
- vapor pressure
- 0.0000008
- time-weighted average exposure limit
- 0.25
- isomeric SMILES
- C1[C@@H]2[C@H]3[C@@H]([C@H]1[C@H]4[C@@H]2O4)[C@]5(C(=C([C@@]3(C5(Cl)Cl)Cl)Cl)Cl)Cl
- canonical SMILES
- C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl
- Commons category
- Dieldrin
via Wikidata · CC0
~11 min read
Article
7 sectionsContents
- Production
- Use
- Metabolism
- Legislation and history
- Australia
- References
- External links
Dieldrin is an organochlorine compound originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels–Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.
Originally developed in the 1940s as an alternative to DDT, dieldrin proved to be a highly effective insecticide and was very widely used during the 1950s to early 1970s. Endrin is a stereoisomer of dieldrin.