4-Vinylcyclohexene

4-Vinylcyclohexene
Names
	IUPAC name 4-Vinylcyclohexene
	Other names Butadiene dimer; 4-Ethenylcyclohexene; 1-Vinyl-3-cyclohexene; 4-Vinyl-1-cyclohexene;
Identifiers
CAS Number	100-40-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	7218 ;
ECHA InfoCard	100.002.590
EC Number	202-848-9;
KEGG	C19310 ;
PubChem CID	7499;
RTECS number	GW6650000;
UNII	212JQJ15PS ;
CompTox Dashboard (EPA)	DTXSID3021437 ;
	InChI InChI=1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 Key: BBDKZWKEPDTENS-UHFFFAOYSA-N ; InChI=1/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 Key: BBDKZWKEPDTENS-UHFFFAOYAZ;
	SMILES C=CC1C\C=C/CC1;
Properties
Chemical formula	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)
Solubility in water	0.05 g/L[1]
Solubility	soluble in benzene, diethyl ether, petroleum ether
Vapor pressure	2 kPa
Refractive index (nD)	1.4639 (20 °C)
Hazards
Safety data sheet	Oxford University
R-phrases (outdated)	R20 R22
NFPA 704 (fire diamond)	3 0
Flash point	21.2 °C (70.2 °F; 294.3 K) [2]
Autoignition; temperature	269 °C (516 °F; 542 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2563 mg/kg (oral, rat)[3]
Related compounds
Related compounds	1,3-Butadiene; Cyclohexene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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 1,3-butadiene dimerizes 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.

Safety

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

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References

Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 8–111. ISBN 0-8493-0594-2.
"4-Vinylcyclohexene" (PDF). IARC. Retrieved 2009-04-19.
"Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. Retrieved 2009-04-19.
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.
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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[hand-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.

[iarc-2] "4-Vinylcyclohexene" (PDF). IARC. Retrieved 2009-04-19.

[ox-3] "Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. Retrieved 2009-04-19.

[thomas-4] 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.

[ioc-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.