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Merck
CN

94950

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
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329770400
EC Number:
202-848-9
Beilstein/REAXYS Number:
1901553
MDL number:
MFCD00001576

Key Documents

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Product Name

4-Vinyl-1-cyclohexene, analytical standard

InChI key

BBDKZWKEPDTENS-UHFFFAOYSA-N

InChI

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

SMILES string

C=CC1CCC=CC1

grade

analytical standard

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

Quality Level

100

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Application

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

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.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

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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

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2179
BCCL2191
BCCG5086
BCCG7880
BCBZ3843

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Inorganic Reactions and Methods, Reactions Catalyzed by Inorganic Compounds (2009)
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
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
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
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)
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