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393193

Sigma-Aldrich

Hydrocinnamaldehyde

technical grade, 90%

Synonym(s):

3-Phenylpropionaldehyde

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About This Item

Linear Formula:
C6H5CH2CH2CHO
CAS Number:
104-53-0
Molecular Weight:
134.18
Beilstein/REAXYS Number:
1071910
EC Number:
203-211-8
MDL number:
MFCD00007021
UNSPSC Code:
12352100
PubChem Substance ID:
24864504
NACRES:
NA.22

grade

technical grade

Quality Level

100

assay

90%

form

liquid

impurities

<5% 3-phenyl-1-propanol

refractive index

n20/D 1.523 (lit.)

bp

97-98 °C/12 mmHg (lit.)

density

1.019 g/mL at 25 °C (lit.)

SMILES string

[H]C(=O)CCc1ccccc1

InChI

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

InChI key

YGCZTXZTJXYWCO-UHFFFAOYSA-N

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General description

Hydrocinnamaldehyde is C=C double bond hydrogenated cinnamaldehyde. It has been synthesized by the selective hydrogenation of C=C double bond of cinnamaldehyde by various methods. Hydrocinnamaldehyde and nitromethane undergoes Henry reaction to form nitroaldols. The C1 and C3 position labelled with 13C of hydrocinnamaldehyde was subjected to mass spectrometry and the fragmentation pattern was elucidated.

Application

Hydrocinnamaldehyde may be used in the synthesis of the following:
  • 2-Chloro hydrocinnamaldehyde by α-chlorination.
  • Mixture of homopropargyl alcohols by kinetic resolution-allenylboration reactions.
  • Mixture of syn- and anti-β-hydroxyallylsilanes by hydroboration of allenylsilane.
  • (2S)-2-Hydroxy-4-phenylbutanenitrile by catalytic asymmetric cyanosilylation.
  • Cinnamaldehyde by dehydrogenation reaction using Pd(TFA)2/4,5-diazafluorenone catalyst.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

203.0 °F - closed cup

flash_point_c

95 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Influence of Preparation Modes on Pt-Ni/CNTs Catalysts Used in the Selective Hydrogenation of Cinnamaldehyde to Hydrocinnamaldehyde.
Li Y, et al
Catalysis Letters, 126(3-4), 280-285 (2008)
Andy S Tsai et al.
Organic letters, 15(7), 1568-1571 (2013-03-15)
A chiral phosphoric acid catalyzed kinetic resolution/allenylboration of racemic allenylboronates with aldehydes is described. Allenylboration of aldehydes with 2.8 equiv of allenylboronate (±)-1 in the presence of 10 mol % of catalyst (R)-2 provided anti-homopropargyl alcohols 3 in 83-95% yield
Ming Chen et al.
Organic letters, 13(8), 1992-1995 (2011-03-18)
The kinetic hydroboration of allenylsilane 5 with ((d)Ipc)(2)BH at -40 °C provides allylborane 9Z with ≥12:1 selectivity. When the hydroboration is performed at temperatures above -40 °C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >20:1 selectivity. Subsequent
Carbon nanofiber supported palladium catalyst for liquid-phase reactions: An active and selective catalyst for hydrogenation of cinnamaldehyde into hydrocinnamaldehyde.
Pham-Huu C, et al
J. Mol. Catal. A: Chem., 170(1), 155-163 (2001)
Enantioselective henry reactions under dual Lewis acid/amine catalysis using chiral amino alcohol ligands.
Claudio Palomo et al.
Angewandte Chemie (International ed. in English), 44(25), 3881-3884 (2005-05-14)
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