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Sigma-Aldrich

1-Vinyl cyclohexanol

97%

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About This Item

Linear Formula:
H2C=CHC6H10OH
CAS Number:
1940-19-8
Molecular Weight:
126.20
EC Number:
217-718-7
MDL number:
MFCD01734994
UNSPSC Code:
12352100
PubChem Substance ID:
24879518
NACRES:
NA.22

assay

97%

refractive index

n20/D 1.478 (lit.)

bp

74 °C/19 mmHg (lit.)

density

0.942 g/mL at 25 °C (lit.)

SMILES string

OC1(CCCCC1)C=C

InChI

1S/C8H14O/c1-2-8(9)6-4-3-5-7-8/h2,9H,1,3-7H2

InChI key

ZXKHOVDDJMJXQP-UHFFFAOYSA-N

General description

1-Vinyl cyclohexanol, also known as 1-vinyl-1-cyclohexanol, is a tertiary allylic alcohol. It can be synthesized from cyclohexanone and vinyl chloride. It can undergo transition-metal-free tandem allylic borylation in the presence of B2pin [bis(pinacolato)diboron], Cs2CO3, THF and MeOH to yield triborated product. Pd-fullerite catalysts have been prepared which effectively catalyzes the hydrogenation of 1-ethynyl-1-cyclohexanol to 1-vinyl-1-cyclohexanol.

Application

1-Vinyl cyclohexanol may be used to synthesize:
  • 1-vinyl-1-cyclohexene
  • 1-vinyl-1-cyclohexylacrylate
  • cyclohexylideneacetaldehyde

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

158.0 °F - closed cup

flash_point_c

70 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Synthesis of spirocyclic butenolides by ring closing metathesis.
Albrecht U and Langer P.
Tetrahedron, 63(22), 4648-4654 (2007)
One-pot rapid low-cost synthesis of Pd-fullerite catalysts.
Chong LC, et al.
Journal of Materials Chemistry, 18(40), 4808-4813 (2008)
Lewis Acid Promoted Oxidative Rearrangement of Tertiary Allylic Alcohols with the PhIO/TEMPO System.
Vatele JM.
Synlett, 12, 1785-1788 (2008)
Transition-Metal-Free Borylation of Allylic and Propargylic Alcohols.
Miralles N, et al.
Angewandte Chemie (International Edition in English), 128(13), 4375-4379 (2016)
Dimerization of conjugated cyclodienes.
Suga K, et al.
Canadian Journal of Chemistry, 45(9), 933-937 (1967)

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