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94950

Supelco

4-Vinyl-1-cyclohexene

analytical standard

Synonym(s):

4-Ethenyl-1-cyclohexene, NSC 15760

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About This Item

Linear Formula:
C6H9CH=CH2
CAS Number:
100-40-3
Molecular Weight:
108.18
Beilstein:
1901553
EC Number:
202-848-9
MDL number:
MFCD00001576
UNSPSC Code:
41116107
PubChem Substance ID:
329770400
NACRES:
NA.24

grade

analytical standard

Quality Level

100

vapor density

3.76 (vs air)

vapor pressure

10.2 mmHg ( 25 °C)

Assay

≥99.5% (GC)

autoignition temp.

517 °F

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.463 (lit.)
n20/D 1.464

bp

126-127 °C (lit.)

mp

−101 °C (lit.)

density

0.831 g/mL at 20 °C
0.831 g/mL at 20 °C
0.832 g/mL at 25 °C (lit.)

application(s)

environmental
petroleum

format

neat

storage temp.

2-8°C

SMILES string

C=CC1CCC=CC1

InChI

1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2

InChI key

BBDKZWKEPDTENS-UHFFFAOYSA-N

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General description

4-Vinyl-1-cyclohexene can be synthesized via cyclo-dimerization of butadiene in the presence of nitrosyl iron catalysts like [Fe(NO)2(CO)2] or [{FeCl(NO)2}2]/reductant.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Carc. 2 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

60.8 °F - closed cup

Flash Point(C)

16 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2179
BCCL2191
BCCG5086
BCCG7880
BCBZ3843

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S M Fontaine et al.
Drug metabolism and disposition: the biological fate of chemicals, 29(9), 1236-1242 (2001-08-15)
4-Vinyl-1-cyclohexene (VCH) is ovotoxic in B6C3F(1) mice but not in Fischer-344 rats, which can be partially attributed to greater formation of toxic epoxides from VCH in mice compared with rats. Since repeated exposure to VCH is necessary to cause ovotoxicity
S M Borman et al.
Toxicology and applied pharmacology, 167(3), 191-198 (2000-09-14)
Extensive destruction of primordial follicles by exposure to ovarian toxicants can cause early menopause in women. Primordial follicle destruction is known to result from dosing of mice and rats with three polycyclic aromatic hydrocarbons (PAHs), contaminants commonly found in cigarette
D A Keller et al.
Toxicology and applied pharmacology, 144(1), 36-44 (1997-05-01)
4-Vinylcyclohexene (4-VCH), the dimer of 1,3-butadiene, is an ovarian toxicant in mice due to the formation of a diepoxide metabolite, but the tissue-specific site of formation of the metabolites is unknown. Microsomal preparations from liver, lung, and ovaries obtained from
Inorganic Reactions and Methods, Reactions Catalyzed by Inorganic Compounds (2009)
S M Fontaine et al.
Drug metabolism and disposition: the biological fate of chemicals, 29(2), 179-184 (2001-02-13)
The racemic mixture of 4-vinylcyclohexene (VCH) forms ovotoxic epoxides [VCH-1,2-epoxide, VCH-7,8-epoxide, and vinylcyclohexene diepoxide (VCD)] by cytochrome P450 (CYP) in B6C3F(1) female mice. These epoxides deplete primordial and primary follicles. The current studies compared in vitro epoxidation of (R)-VCH with
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