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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:
1071910
EC Number:
203-211-8
MDL number:
MFCD00007021
UNSPSC Code:
12352100
PubChem Substance ID:
24864504
NACRES:
NA.22

grade

technical grade

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 Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

203.0 °F - closed cup

Flash Point(C)

95 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
Hydrogenation of cinnamaldehyde using catalysts prepared from supported palladium phosphine complexes.
Cairns GR, et al
J. Catal., 166(1), 89-97 (1997)
Tianning Diao et al.
Chemical science, 3, 887-891 (2012-06-13)
The direct α, β-dehydrogenation of aldehydes and ketones represents an efficient alternative to stepwise methods to prepare enal and enone products. Here, we describe a new Pd(TFA)(2)/4,5-diazafluorenone dehydrogenation catalyst that overcomes key limitations of previous catalyst systems. The scope includes
Elucidation of elctron-impact-induced fragmentations of hydrocinnamaldehyde by 13C labelling; evidence for an 'ortho attack'in the molecular ion.
Venema A and Nibbering NMM
Org. Mass Spectrom., 9(6), 628-630 (1974)
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
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