Structure via PubChem · Public domain (PubChem)
heptachlor
Sign in to saveAlso known as 1,4,5,6,7,8,8-Heptachloro-3a,4,7,7a-tetrahydro-4,7-methanoindene, Heptachlorane, 1,5,7,8,9,10,10-heptachlorotricyclo[5.2.1.0(2,6)]deca-3,8-diene, 3-chlorochlordene, Heptamul, 1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene
Heptachlor is an organochlorine compound that was used as an insecticide. Usually sold as a white or tan powder, heptachlor is one of the cyclodiene insecticides. In 1962, Rachel Carson's Silent Spring questioned the safety of heptachlor and other chlorinated insecticides. Due to its highly stable structure, heptachlor can persist in the environment for decades. In the United States, the Environmental Protection Agency has limited the sale of heptachlor products to the specific application of fire ant control in underground transformers. The amount that can be present in different foods is reg
Chemical data
- Formula
- C10H5Cl7
- Molecular weight
- 373.3 g/mol
- IUPAC name
- 1,5,7,8,9,10,10-heptachlorotricyclo[5.2.1.02,6]deca-3,8-diene
- SMILES
- C1=CC(C2C1C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl)Cl
- InChIKey
- FRCCEHPWNOQAEU-UHFFFAOYSA-N
- XLogP
- 4.3
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Research
1,668 papers- Chlordane and heptachlor.IARC monographs on the evaluation of carcinogenic risks to humans · 1991
- Ecological toxicology and human health effects of heptachlor.Reviews of environmental contamination and toxicology · 1990
- Heptachlor and heptachlor epoxide.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1979
- Heptachlor and heptachlor epoxide.Reviews of environmental contamination and toxicology · 1988
- Heptachlor-induced epithelial to mesenchymal transition in HK-2 cells mediated via TGF-β1/Smad signalling.Human & experimental toxicology · 2019
via PubMed
Wikidata facts
- Mass
- 369.82109392
Show 12 more facts
- chemical formula
- C₁₀H₅Cl₇
- NIOSH Pocket Guide ID
- 0311
- density
- 1.66
- immediately dangerous to life or health
- 35
- melting point
- 203
- decomposition point
- 293
- vapor pressure
- 0.0003
- solubility
- 0.0006
- time-weighted average exposure limit
- 0.5
- canonical SMILES
- C1=CC(C2C1C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl)Cl
- MCN code
- 2903.82.30
- Commons category
- Heptachlor
via Wikidata · CC0
~5 min read
Article
8 sectionsContents
- Synthesis
- Metabolism
- Environmental impact
- Toxicity of heptachlor and related derivatives
- Human impact
- Chemical properties
- References
- External links
Heptachlor is an organochlorine compound that was used as an insecticide. Usually sold as a white or tan powder, heptachlor is one of the cyclodiene insecticides. In 1962, Rachel Carson's Silent Spring questioned the safety of heptachlor and other chlorinated insecticides. Due to its highly stable structure, heptachlor can persist in the environment for decades. In the United States, the Environmental Protection Agency has limited the sale of heptachlor products to the specific application of fire ant control in underground transformers. The amount that can be present in different foods is regulated.
==Synthesis== Analogous to the synthesis of other cyclodienes, heptachlor is produced via the Diels-Alder reaction of hexachlorocyclopentadiene and cyclopentadiene. The resulting adduct is chlorinated followed by treatment with hydrogen chloride in nitromethane in the presence of aluminum trichloride or with iodine monochloride.