Norbornene
From Wikipedia, the free encyclopedia
| Norbornene | |
|---|---|
| Chemical name | Bicyclo[2.2.1]-2-heptene |
| Chemical formula | C7H10 |
| InChI | InChI=1/C7H10/c1-2-7-4-3-6
(1)5-7/h1-2,6-7H,3-5H2 |
| Molecular mass | 94.15 g/mol |
| Melting point | 42-46 °C |
| Boiling point | 96 °C |
| Density | g/cm3 |
| CAS number | 498-66-8 |
| SMILES | C\1=C\C2CC/1CC2 |
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| Disclaimer and references | |
Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring bridged with a methylene group in the para position. The molecule carries a double bond which induces significant ring strain and significant reactivity.
Norbornene, and many of its derivatives, is made by a Diels-Alder reaction of cyclopentadiene and ethylene. Related bicyclics are norbornadiene which has the same carbon skeleton but with two double bonds and norbornane which is completely saturated without double bonds.
Norbornene undergoes an acid-catalyzed hydration reaction with water to form norborneol.
[edit] Polynorbornenes
Norbornenes are important monomers in ring-opening metathesis polymerizations (ROMP) with for instance the Grubbs' catalyst. Polynorbornenes are polymers with high glass transition temperatures and high optical clarity.
In addition to ROMP polymerization, norbornene monomers also undergo vinyl-addition polymerization.
Ethylidene norbornene is a related monomer derived from cyclopentadiene and butadiene.
[edit] External links
- Norbornene MSDS
- Norbornene MSDS II
- Norbornene industrial supplier
- endo Tricyclo[3.2.1.02,4]oct-6-ene by reaction of cyclopropene and cyclopentadiene in Organic Syntheses Coll. Vol. 10, p.231; Vol. 77, p.254 Article
- endo-Tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione from benzoquinone and cyclopentadiene in Organic Syntheses Article
