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393193

Sigma-Aldrich

Hydrocinnamaldehyde

technical grade, 90%

Sinonimo/i:

3-Phenylpropionaldehyde

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About This Item

Formula condensata:
C6H5CH2CH2CHO
Numero CAS:
Peso molecolare:
134.18
Beilstein:
1071910
Numero CE:
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22

Grado

technical grade

Livello qualitativo

Saggio

90%

Stato

liquid

Impurezze

<5% 3-phenyl-1-propanol

Indice di rifrazione

n20/D 1.523 (lit.)

P. ebollizione

97-98 °C/12 mmHg (lit.)

Densità

1.019 g/mL at 25 °C (lit.)

Gruppo funzionale

aldehyde
phenyl

Stringa SMILE

[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
YGCZTXZTJXYWCO-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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.

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

203.0 °F - closed cup

Punto d’infiammabilità (°C)

95 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Metal versus silyl triflate catalysis in the Mukaiyama aldol addition reaction.
Carreira EM and Singer RA
Tetrahedron Letters, 35(25), 4323-4326 (1994)
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)
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)
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
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)

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