Structure via PubChem · Public domain (PubChem)
mirex
Sign in to saveAlso known as dodecachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalene, perchloropentacyclo[5.2.1.0(2,6).0(3,9).0(5,8)]decane, CG-1283, perchloropentacyclodecane, perchlorodihomocubane, 1,2,3,4,5,5,6,7,8,9,10,10-dodecachloropentacyclo[5.3.0.0(2,6).0(3,9).0(4,8)]decane, dodecachloropentacyclo[5.3.0.0^{2,6}.0^{3,9}.0^{4,8}]decane
Mirex is an organochloride that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of both cyclopentadiene and cubane. It was popularized to control fire ants but by virtue of chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. The spread of the red imported fire ant was encouraged by the use of mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976. It is
Chemical data
- Formula
- C10Cl12
- Molecular weight
- 545.5 g/mol
- IUPAC name
- 1,2,3,4,5,5,6,7,8,9,10,10-dodecachloropentacyclo[5.3.0.02,6.03,9.04,8]decane
- SMILES
- C12(C3(C4(C5(C3(C(C1(C5(C2(C4(Cl)Cl)Cl)Cl)Cl)(Cl)Cl)Cl)Cl)Cl)Cl)Cl
- InChIKey
- GVYLCNUFSHDAAW-UHFFFAOYSA-N
- XLogP
- 5.3
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 539.62623216
Show 3 more facts
- chemical formula
- C₁₀Cl₁₂
- canonical SMILES
- C12(C3(C4(C5(C3(C(C1(C5(C2(C4(Cl)Cl)Cl)Cl)Cl)(Cl)Cl)Cl)Cl)Cl)Cl)Cl
- Commons category
- Mirex
via Wikidata · CC0
~6 min read
Article
7 sectionsContents
- Production and applications
- Degradation
- Bioaccumulation and biomagnification
- Safety
- Health effects
- References
- Further reading
Mirex is an organochloride that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of both cyclopentadiene and cubane. It was popularized to control fire ants but by virtue of chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. The spread of the red imported fire ant was encouraged by the use of mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976. It is prohibited by the Stockholm Convention on Persistent Organic Pollutants.
==Production and applications== Mirex was first synthesized in 1946, but was not used in pesticide formulations until 1955. Mirex was produced by the dimerization of hexachlorocyclopentadiene in the presence of aluminium chloride.