Endrin
Overview
 
Endrin is an organochloride
Organochloride
An organochloride, organochlorine, chlorocarbon, chlorinated hydrocarbon, or chlorinated solvent is an organic compound containing at least one covalently bonded chlorine atom. Their wide structural variety and divergent chemical properties lead to a broad range of applications...

 that was primarily used as an insecticide
Insecticide
An insecticide is a pesticide used against insects. They include ovicides and larvicides used against the eggs and larvae of insects respectively. Insecticides are used in agriculture, medicine, industry and the household. The use of insecticides is believed to be one of the major factors behind...

. It is a colourless odorless solid, although commercial samples are often off-white. It is also a rodenticide. This compound became infamous as persistent organic pollutant
Persistent organic pollutant
thumb|right|275px|State parties to the Stockholm Convention on Persistent Organic PollutantsPersistent organic pollutants are organic compounds that are resistant to environmental degradation through chemical, biological, and photolytic processes...

 and for this reason is banned in many countries.
Endrin is produced via a multistep route from hexachlorocyclopentadiene
Hexachlorocyclopentadiene
Hexachlorocyclopentadiene is an organochlorine compound that is a precursor to several pesticides. This colourless liquid is an inexpensive reactive diene. Many of its derivatives proved to be highly controversial, as studies showed them to be persistent organic pollutants. Collectively, the...

. Diels-Alder addition of acetylene gives an isomer of hexachloronorbornadiene. This compound undergoes a second Diels-Alder addition, this time with cyclopentadiene
Cyclopentadiene
Cyclopentadiene is an organic compound with the formula C5H6. This colorless liquid has a strong and unpleasant odor. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a Diels–Alder reaction...

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