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Ethylidene norbornene

Chemical compound From Wikipedia, the free encyclopedia

Ethylidene norbornene
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Ethylidene norbornene (ENB) is an organic compound that consists of an ethylidene (CH3C(H)=) group attached to norbornene. It is a colorless liquid. The molecule consists of two sites of unsaturation. The compound consists of (E)- and (Z)-stereoisomers, but the mixtures are typically not separated.

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Preparation and use

It is prepared by isomerization of vinyl norbornene, which in turn is obtained by the Diels-Alder reaction of butadiene and cyclopentadiene.[1]

Ethylidene norbornene can be produced in two steps from cyclopentadiene.

It is a monomer that used in the production of the commercial polymer EPDM. Only the ring alkene participates in the copolymerization. The exocyclic double bond (the ethylidene group) undergoes sulfur vulcanization.

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Safety

Its LD50 (intravenous, rabbit) ranges from 0.09 (male rabbit) to 0.11 ml/kg (female). It is also a neurotoxin.[2]

References

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