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 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL3186510

ChemSpider |

* 17262

EC Number |

* 221-259-8

PubChem CID

* 18273

UNII |

* O26JW4DH9I Y

CompTox Dashboard (EPA)

* DTXSID6029250

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

Tracking categories (test):

* SizeSet

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

-1">50 is 0.10–0.05 mg/kg (intravenous, female rabbit). It is also a neurotoxin.[2]

## References

1. ↑ Behr, Arno (2000). 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.

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*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency