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108197

Sigma-Aldrich

Cinnamyl alcohol

98%

Synonym(s):

3-Phenyl-2-propen-1-ol

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About This Item

Linear Formula:
C6H5CH=CHCH2OH
CAS Number:
104-54-1
Molecular Weight:
134.18
Beilstein/REAXYS Number:
1903999
EC Number:
203-212-3
MDL number:
MFCD00002921
UNSPSC Code:
12352100
PubChem Substance ID:
24846655
NACRES:
NA.22

vapor density

4.6 (vs air)

Quality Level

100

vapor pressure

<0.01 mmHg ( 25 °C)

assay

98%

form

liquid

bp

250 °C (lit.)

mp

30-33 °C (lit.)

solubility

H2O: soluble
alcohol: freely soluble
diethyl ether: freely soluble
glycerol: soluble
organic solvents: freely soluble

density

1.044 g/mL at 25 °C (lit.)

SMILES string

OC\C=C\c1ccccc1

InChI

1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+

InChI key

OOCCDEMITAIZTP-QPJJXVBHSA-N

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General description

Cinnamyl alcohol is an organic building block used as a chain transfer agent in polymerization. Cinnamyl alcohol causes Friedel Crafts alkylation of bulky aromatic compound 2,4-di-tert-butylphenol using mesoporous aluminosilicate as catalyst. It undergoes partial oxidation in air to form cinnamaldehyde over a series of Bi-Pt/alumina catalysts. It is also used in perfumery and in deodorant compositions.

Application

Cinnamyl alcohol was used to study the alkylation of 2,4-di-tert-butylphenol by cinnamyl alcohol using aluminum-containing mesoporous ethane-silica catalyst. It was used to study gold nanoparticles supported on titanium dioxide catalysed oxidative coupling of alcohols and amines to form the corresponding imines.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

258.8 °F - closed cup

flash_point_c

126 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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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Mesoporous aluminosilicate MCM-41 as a convenient acid catalyst for Friedel-Crafts alkylation of a bulky aromatic compound with cinnamyl alcohol.
Armengol E, et al.
Journal of the Chemical Society. Chemical Communications, 5, 519-520 (1995)
Hydrothermal stability and catalytic activity of aluminum-containing mesoporous ethane-silicas.
Yang Q, et al.
The Journal of Physical Chemistry B, 108(23), 7934-7937 (2004)
Selective oxidation of cinnamyl alcohol to cinnamaldehyde with air over Bi-Pt/alumina catalysts.
Mallat T, et al.
J. Catal., 153(1), 131-143 (1995)
Formation of imines by selective gold-catalysed aerobic oxidative coupling of alcohols and amines under ambient conditions.
Kegnaes S, et al.
Green Chemistry, 12(8), 1437-1441 (2010)
Laura Fitzpatrick et al.
Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology, 40(1), 10-13 (2010-10-26)
Food-associated allergies, especially to benzoates and cinnamon-related compounds, have been associated with orofacial granulomatosis and both standard and urticarial patch testing have been used to detect such allergies. Elimination diets have also been shown to be effective in some patients.
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