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Merck
CN

V2208

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
EC Number:
202-848-9
UNSPSC Code:
12162002
PubChem Substance ID:
329829033
Beilstein/REAXYS Number:
1901553
MDL number:
MFCD00001576

Key Documents

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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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Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

60.8 °F - closed cup

flash_point_c

16 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
S27637
22413LY
16221BR
13209BS
11528MF

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Jodi A Flaws et al.
Toxicology and applied pharmacology, 215(1), 51-56 (2006-04-25)
The occupational chemical 4-vinylcyclohexene (VCH) destroys small preantral ovarian follicles in mice following repeated daily dosing. The cell survival gene bcl-2 is thought to protect against follicular death during embryogenesis because primordial follicle numbers in newborn bcl-2 overexpressing (OE) mice
C Chiappe et al.
Chemical research in toxicology, 14(5), 492-499 (2001-05-23)
The stereochemical course of the biotransformation of 4-vinylcyclohexene (VCH, 1) by liver microsomes from male and female control and induced rats and purified rat P450 2B1 and 2E1 has been determined. The epoxidation of 1, catalyzed by male microsomes, occurs
P J Devine et al.
Frontiers in bioscience : a journal and virtual library, 7, d1979-d1989 (2002-08-06)
Many investigations have utilized techniques for culturing ovarian tissue or isolated follicles in vitro. Whole ovaries from fetal or neonatal rodents have been incubated in organ culture systems. This has been utilized to understand the sequence of follicle formation and
P B Hoyer et al.
Annual review of pharmacology and toxicology, 36, 307-331 (1996-01-01)
The ovary plays a pivotal role in the regulation of reproductive function in females. Development, maturation, and ovulation of oocytes occur within ovarian follicles. Females are born with a finite number of undeveloped, primordial follicles. Chemicals that destroy oocytes contained
J K Doerr-Stevens et al.
Drug metabolism and disposition: the biological fate of chemicals, 27(2), 281-287 (1999-02-04)
4-Vinylcyclohexene (VCH), an ovarian toxicant in mice, is known to irreversibly deplete ovarian follicles as a consequence of VCH diepoxide formation. Because ovotoxicity requires repeated dosing of VCH, the effect of consecutive daily doses of VCH (7.5 mmol/kg/day) on mouse
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