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Norbornene

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Norbornene
Names
IUPAC name Bicyclohept-2-ene
Other names Norbornylene
Norcamphene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.152 Edit this at Wikidata
EC Number
  • 207-866-0
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H10/c1-2-7-4-3-6(1)5-7/h1,7H,2-5H2Key: VGUXWSJVGWCTEC-UHFFFAOYSA-N
  • InChI=1/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2
  • InChI=1/C7H10/c1-2-7-4-3-6(1)5-7/h1,7H,2-5H2Key: VGUXWSJVGWCTEC-UHFFFAOYAW
SMILES
  • C1/C2=C\CC1CC2
Properties
Chemical formula C7H10
Molar mass 94.157 g·mol
Appearance White solid
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2 3 1
Flash point −15 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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, like 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. This reaction is of great interest to chemists studying non-classical ions.

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.

Norbornene ROMP

In addition to ROMP polymerization, norbornene monomers also undergo vinyl-addition polymerization.

Ethylidene norbornene is a related monomer derived from cyclopentadiene and butadiene.

Practical uses

Norbornene does not have as many practical uses as ethylene or other commodity chemicals. It is utilized to make pharmaceutical intermediates, pesticide compounds, specialty fragrances and in general organic synthesis. When combined with ethylene, norbornene will react and turn into a cyclic olefin copolymer.

Polynorbornene, known under Norsorex, a brand from Astrotech Advanced Elastomerproducts GmbH since 2008, is used mainly in the rubber industry for anti-vibration (rail, building, industry), anti-impact (personal protective equipment, shoe parts, bumpers) and grip improvement (toy tires, racing tires, transmission systems, transports systems for copiers, feeders, etc.)

  • Reachable performances: Loss factors (tan delta) larger than 3, rebounds of less than 1%, tear strengths of 50 N/mm², friction coefficients of 2 and more, Shore hardness between 4 and 90 Shore A.
  • Second main application: oil-binding system with absorption capability of hydrocarbons, 10 times of own weight

References

  1. Norbornene MSDS
  2. Paul Binger, Petra Wedemann, and Udo H. Brinker. "Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 10, p. 231.
  3. Masaji Oda, Takeshi Kawase, Tomoaki Okada, and Tetsuya Enomoto. "2-Cyclohexene-1,4-dione". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 9, p. 186.
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