4-Vinylcyclohexene

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4-Vinylcyclohexene
4-Vinylcyclohexene
Names
Preferred IUPAC name
4-Ethenylcyclohex-1-ene
Other names
  • Butadiene dimer
  • 4-Ethenylcyclohexene
  • 1-Vinyl-3-cyclohexene
  • 4-Vinyl-1-cyclohexene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.590 Edit this at Wikidata
EC Number
  • 202-848-9
KEGG
RTECS number
  • GW6650000
UNII
  • InChI=1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 checkY
    Key: BBDKZWKEPDTENS-UHFFFAOYSA-N checkY
  • InChI=1/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2
    Key: BBDKZWKEPDTENS-UHFFFAOYAZ
  • C=CC1C\C=C/CC1
Properties
C8H12
Molar mass 108.184 g·mol−1
Appearance Colorless liquid
Density 0.8299 g/cm3 at 20°C
Melting point −108.9 °C (−164.0 °F; 164.2 K)
Boiling point 128.9 °C (264.0 °F; 402.0 K)
0.05 g/L[1]
Solubility soluble in benzene, diethyl ether, petroleum ether
Vapor pressure 2 kPa
1.4639 (20 °C)
Hazards
GHS labelling:
GHS08: Health hazard
Warning
H351
P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 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 (yellow): no hazard codeSpecial hazards (white): no code
0
3
Flash point 21.2 °C (70.2 °F; 294.3 K)[3]
269 °C (516 °F; 542 K)
Lethal dose or concentration (LD, LC):
2563 mg/kg (oral, rat)[2]
Safety data sheet (SDS) Oxford University
Related compounds
Related compounds
 Buta-1,3-diene
Cyclohexene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

4-Vinylcyclohexene is an organic compound consisting of a vinyl group attached to the 4-position of the cyclohexene ring. It is a colorless liquid. Although chiral, it is used mainly as the racemate. It is a precursor to vinylcyclohexene dioxide.[4]

Production

It is produced by buta-1,3-diene dimerization in a Diels-Alder reaction.[5][4] The reaction is conducted at 110 - 425 °C at pressures of 1.3 - 100 MPa in the presence of a catalyst. A mixture of silicon carbide and salts of copper or chromium comprises the catalyst. A competing product is 1,5-cyclooctadiene.

1,3-Butadiene undergoes a Diels-Alder cycloaddition reaction to form 4-vinylcyclohexane.

Safety

4-Vinylcyclohexene is classified as a Group 2B carcinogen by the IARC ("possibly carcinogenic to humans").[3]

References

  1. ^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 8–111. ISBN 0-8493-0594-2.
  2. ^ "Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. Archived from the original on 2010-12-31. Retrieved 2009-04-19.
  3. ^ a b "4-Vinylcyclohexene" (PDF). IARC. Retrieved 2009-04-19.
  4. ^ a b Schiffer, Thomas; Oenbrink, Georg. "Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_205.pub2. ISBN 978-3527306732.
  5. ^ Wittcoff, Harold; Reuben, B. G.; Plotkin, Jeffrey S. (1998). Industrial Organic Chemicals (2 ed.). Wiley-Interscience. pp. 236–7. ISBN 978-0-471-44385-8. Retrieved 2009-04-19.
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