4-Vinylcyclohexene

4-Vinylcyclohexene

IUPAC name 4-Vinylcyclohexene
Other names Butadiene dimer, 4-ethenylcyclohexene, 1-vinyl-3-cyclohexene; 4-vinyl-1-cyclohexene
Identifiers
CAS number	100-40-3^Y
PubChem	7499
ChemSpider	7218^Y
KEGG	C19310^N
RTECS number	GW6650000
Jmol-3D images	Image 1
SMILES C=CC1C\C=C/CC1
InChI InChI=1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2^Y Key: BBDKZWKEPDTENS-UHFFFAOYSA-N^Y InChI=1/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 Key: BBDKZWKEPDTENS-UHFFFAOYAZ
Properties
Molecular formula	C₈H₁₂
Molar mass	108.181 g/mol
Appearance	colorless liquid
Density	0.8299 g/cm³ at 20°C
Melting point	-108.9°C
Boiling point	128.9°C
Solubility in water	0.05 g/L^[1]
Solubility	soluble in benzene, diethyl ether, petroleum ether
Vapor pressure	2 kPa at 25°C
Hazards
MSDS	Oxford University
EU Index	Harmful (Xn)
R-phrases	R20 R22
Flash point	21.2°C^[2]
LD₅₀	2563 mg/kg (oral, rat)^[3]
Related compounds
Related compounds	1,3-Butadiene Cyclohexene
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

4-Vinylcyclohexene is an organic compound formed when 1,3-butadiene dimerizes in a Diels-Alder reaction^[4]. It is found in industrial processes involving 1,3-butadiene, including the manufacture of lauric acid. The 4-vinylcyclohexene formed may be sold as-is or converted to 4-vinylcyclohexene diepoxide.

Reactions

Industrially, 4-vinylcyclohexene is manufactured by dimerizing 1,3-butadiene at 110 - 425°C at pressures of 1.3 - 100 MPa over silicon carbide and salts of copper or chromium.

Safety

4-Vinylcyclohexene is classified as a Group 2B carcinogen by the IARC ^[2].

References

^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. pp. 8–111. ISBN 0-8493-0594-2.
^ ^a ^b "4-Vinylcyclohexene". IARC. http://monographs.iarc.fr/ENG/Monographs/vol60/mono60-13.pdf. Retrieved 2009-04-19.
^ "Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. http://msds.chem.ox.ac.uk/VI/4-vinylcyclohexene.html. Retrieved 2009-04-19.
^ 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. http://books.google.com/?id=4KHzc-nYPNsC&pg=PA236&dq=4-vinylcyclohexene+diels-alder. Retrieved 2009-04-19.