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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:
42273-76-7
Molecular Weight:
134.18
MDL number:
MFCD00093987
UNSPSC Code:
12352100
PubChem Substance ID:
24866527
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

Related Categories

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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)
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

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