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Sigma-Aldrich

Cinnamyl alcohol

98%

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Synonym(s):
3-Phenyl-2-propen-1-ol
Linear Formula:
C6H5CH=CHCH2OH
CAS Number:
104-54-1
Molecular Weight:
134.18
Beilstein:
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

Signal Word

Warning

Hazard Statements

H302,H317,H411

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(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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RIFM fragrance ingredient safety assessment, cinnamyl alcohol, CAS Registry Number 104-54-1
AM Api, et al.
Food And Chemical Toxicology, 141, 111337-111337 (2020)
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)
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