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423769

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
NACRES:
NA.22
PubChem Substance ID:
24866527
UNSPSC Code:
12352100
MDL number:
MFCD00093987
Assay:
97%
Form:
liquid
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Quality Level

200

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.)

functional group

hydroxyl, phenyl

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

201.2 °F - closed cup

flash_point_c

94 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
0000331374
0000331375
0000331375
0000331374
0000275150

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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
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)
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Global Trade Item Number

SKUGTIN
423769-10G04061837332418
423769-1G04061837332425