4-Vinylcyclohexene

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]

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
CAS Number	100-40-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82377
ChEMBL	ChEMBL1330194
ChemSpider	7218 Y
ECHA InfoCard	100.002.590
EC Number	202-848-9
KEGG	C19310 Y
PubChem CID	7499
RTECS number	GW6650000
UNII	212JQJ15PS N
CompTox Dashboard (EPA)	DTXSID3021437
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
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
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H351
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)	0 3
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]
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 YN ?) Infobox references

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.

In North America this is produced by Nippon Chemical Texas Inc. in Pasadena, TX.

Safety

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