Vinyl norbornene

From Wikipedia, the free encyclopedia
Vinyl norbornene
VNB.svg
Names
IUPAC name
5-Ethenylbicyclo[2.2.1]hept-2-ene
Other names
2-Ethylidene-5-norbornene; 5-Vinyl-2-norbornene
Identifiers
3D model (JSmol)
UNII
  • 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
  • C=CC1CC2CC1C=C2
Properties
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).

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[edit]

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

References[edit]

  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. PMID 9285533. S2CID 21154862.{{cite journal}}: CS1 maint: uses authors parameter (link)