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423769

Sigma-Aldrich

α-Vinylbenzyl alcohol

97%

Synonym(s):

α-Ethenylbenzenemethanol, α-Phenylallyl alcohol, (±)-1-Phenylallyl alcohol, 1-Hydroxy-1-phenyl-2-propene, 1-Phenyl-2-propen-1-ol, 1′-Hydroxyallylbenzene, 3-Phenyl-3-hydroxy-1-propene, Phenylvinylcarbinol

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About This Item

Linear Formula:
C6H5CH(CH=CH2)OH
CAS Number:
Molecular Weight:
134.18
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.54 (lit.)

bp

101-102 °C/12 mmHg (lit.)

density

1.021 g/mL at 25 °C (lit.)

SMILES string

OC(C=C)c1ccccc1

InChI

1S/C9H10O/c1-2-9(10)8-6-4-3-5-7-8/h2-7,9-10H,1H2

InChI key

MHHJQVRGRPHIMR-UHFFFAOYSA-N

General description

α-Vinylbenzyl alcohol is an allyl alcohol derivative. Its isomerization reaction using a novel ternary catalyst system has been reported. The kinetic resolution of racemic α-vinylbenzyl alcohol by tungsten-catalyzed asymmetric epoxidation method has been repoorted. The coupling reaction of α-vinylbenzyl alcohol and aldehydes in the presence of RuCl2(PPh3)3 catalyst and In(OAc)3 as a co-catalyst in ionic liquids has been investigated. Etherification reaction of glycerol with α-vinylbenzyl alcohol in the presence of sulfonic catalyst immobilized on silica (SiO2–SO3H) has been reported.

Application

α−Vinylbenzyl alcohol may be used in the synthesis of cinnamyl ethers by reacting with alcohols.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

201.2 °F - closed cup

Flash Point(C)

94 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

423769-10G:
423769-BULK:
423769-1G:
423769-VAR:


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Heterogeneously catalyzed etherification of glycerol: new pathways for transformation of glycerol to more valuable chemicals.
Gu Y, et al.
Green Chemistry, 10(2), 164-167 (2008)
Yoshio Kasashima et al.
Journal of oleo science, 59(10), 549-555 (2010-09-30)
Reactions of α-vinylbenzyl alcohol with other alcohols using iodine as a catalyst were investigated. The corresponding cinnamyl ethers were obtained as products. This suggested that α-vinylbenzyl alcohol was converted to cinnamyl ethers via 1-phenylallyl cation. Cinnamyl ethyl ether was obtained
Masato Ito et al.
Journal of the American Chemical Society, 127(17), 6172-6173 (2005-04-28)
Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH2-kappa2-P,N]-KOt-Bu (Cp* = eta5-C5(CH3)5) under mild conditions. Mechanistic consideration based on isotope-labeling experiments indicated the present reaction is applicable to the asymmetric isomerization of
Ruthenium-catalyzed tandem olefin migration-Aldol-and mannich-type reactions in ionic liquid.
Yang XF, et al.
J. Mol. Catal. A: Chem., 214(1), 147-154 (2004)
Chuan Wang et al.
Journal of the American Chemical Society, 136(4), 1222-1225 (2014-01-16)
A simple, efficient, and environmentally friendly asymmetric epoxidation of primary, secondary, tertiary allylic, and homoallylic alcohols has been accomplished. This process was promoted by a tungsten-bishydroxamic acid complex at room temperature with the use of aqueous 30% H2O2 as oxidant

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