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V2208

Sigma-Aldrich

4-Vinyl-1-cyclohexene

99%

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:
12162002
PubChem Substance ID:
329829033
Pricing and availability is not currently available.

vapor density

3.76 (vs air)

vapor pressure

10.2 mmHg ( 25 °C)

Assay

99%

autoignition temp.

517 °F

contains

25-200 ppm p-tert-butylcatechol as inhibitor

refractive index

n20/D 1.463 (lit.)

bp

126-127 °C (lit.)

mp

−101 °C (lit.)

density

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

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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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
S27637
03112HY
22413LY
16221BR
13209BS

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Patricia B Hoyer et al.
Birth defects research. Part B, Developmental and reproductive toxicology, 80(2), 113-125 (2007-03-08)
The occupational chemical 4-vinylcyclohexene (VCH) has been shown to cause destruction of small pre-antral follicles in ovaries of mice. Further, its monoepoxide metabolites, 1,2-VCH epoxide, 7,8-VCH epoxide, and the diepoxide, VCD, have been shown to cause pre-antral follicle loss in
Cinzia Chiappe et al.
Chemical research in toxicology, 16(1), 56-65 (2003-04-16)
The stereochemical course of the biotransformation of 1,2-monoepoxides of 4-vinylcyclohexene (2 and 3) by liver microsomes from control and induced rats and by purified P4502B1 and P4502E1 has been determined. The epoxidation of monoexpodies cis-4-vinylcyclohexene 1,2-epoxide (2) and trans-4-vinylcyclohexene 1,2-epoxide
Gold(I)-catalyzed asymmetric cycloisomerization of eneallenes into vinylcyclohexenes.
Michael A Tarselli et al.
Angewandte Chemie (International ed. in English), 46(35), 6670-6673 (2007-07-31)
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
Ellen A Cannady et al.
Toxicological sciences : an official journal of the Society of Toxicology, 73(2), 423-430 (2003-04-18)
4-Vinylcyclohexene (VCH), an occupational chemical, causes destruction of small preantral follicles (F1) in mice. Previous studies suggested that VCH is bioactivated via cytochromes P450 (CYP450) to the ovotoxic, diepoxide metabolite, VCD. Whereas hepatic CYP450 isoforms 2E1, 2A, and 2B can
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