Vinyl norbornene

Vinyl norbornene
Names
	IUPAC name 5-Ethenylbicyclo[2.2.1]hept-2-ene
	Other names 2-Ethylidene-5-norbornene; 5-Vinyl-2-norbornene
Identifiers
CAS Number	3048-64-4;
3D model (JSmol)	Interactive image;
PubChem CID	18273;
	InChI InChI=1S/C9H12/c1-2-8-5-7-3-4-9(8)6-7/h2-4,7-9H,1,5-6H2 Key: INYHZQLKOKTDAI-UHFFFAOYSA-N;
	SMILES C=CC1CC2CC1C=C2;
Properties
Chemical formula	C9H12
Molar mass	120.195 g·mol−1
Appearance	Colorless liquid
Boiling point	141 °C (286 °F; 414 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Vinyl norbornene (VNB) is an organic compound that consists of a vinyl group attached to norbornene. It is a colorless liquid. The compound exists as endo and exo isomers, but these are not typically separated. It is an intermediate in the production of the commercial polymer EPDM. It is prepared by the Diels-Alder reaction of butadiene and cyclopentadiene.[1]

Vinyl norbornene is an intermediate in the production ethylidene norbornene.

Safety

LD₅₀ (intravenous, rabbit = 0.10–0.05 mg/kg(female). It is also a neurotoxin.[2]

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References

Behr, Arno (2000). "Organometallic Compounds and Homogeneous Catalysis". Ullmann's Encyclopedia of Industrial Chemistry. p. 10. doi:10.1002/14356007.a18_215. ISBN 978-3527306732.
Ballantyne, Bryan; Myers, Roy C.; Klonne, Dennis R. (1997). "Comparative acute toxicity and primary irritancy of the ethylidene and vinyl isomers of norbornene". Journal of Applied Toxicology. 17 (4): 211–221. doi:10.1002/(SICI)1099-1263(199707)17:4<211::AID-JAT430>3.0.CO;2-X.CS1 maint: uses authors parameter (link)

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[1] Behr, Arno (2000). "Organometallic Compounds and Homogeneous Catalysis". Ullmann's Encyclopedia of Industrial Chemistry. p. 10. doi:10.1002/14356007.a18_215. ISBN 978-3527306732.

[2] Ballantyne, Bryan; Myers, Roy C.; Klonne, Dennis R. (1997). "Comparative acute toxicity and primary irritancy of the ethylidene and vinyl isomers of norbornene". Journal of Applied Toxicology. 17 (4): 211–221. doi:10.1002/(SICI)1099-1263(199707)17:4<211::AID-JAT430>3.0.CO;2-X.CS1 maint: uses authors parameter (link)