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423769

Sigma-Aldrich

α-Vinylbenzyl alcohol

97%

Synonyme(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

Formule linéaire :
C6H5CH(CH=CH2)OH
Numéro CAS:
42273-76-7
Poids moléculaire :
134.18
Numéro MDL:
MFCD00093987
Code UNSPSC :
12352100
ID de substance PubChem :
24866527
Nomenclature NACRES :
NA.22

Pureté

97%

Forme

liquid

Indice de réfraction

n20/D 1.54 (lit.)

Point d'ébullition

101-102 °C/12 mmHg (lit.)

Densité

1.021 g/mL at 25 °C (lit.)

Chaîne SMILES 

OC(C=C)c1ccccc1

InChI

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

Clé InChI

MHHJQVRGRPHIMR-UHFFFAOYSA-N

Catégories apparentées

Description générale

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

201.2 °F - closed cup

Point d'éclair (°C)

94 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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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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