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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

CHF 97.40


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Grado

technical grade

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.[1][2][3][4][5] Hydrocinnamaldehyde and nitromethane undergoes Henry reaction to form nitroaldols.[6] The C1 and C3 position labelled with 13C of hydrocinnamaldehyde was subjected to mass spectrometry and the fragmentation pattern was elucidated.[7]

Applicazioni

Hydrocinnamaldehyde may be used in the synthesis of the following:
  • 2-Chloro hydrocinnamaldehyde by α-chlorination.[8]
  • Mixture of homopropargyl alcohols by kinetic resolution-allenylboration reactions.[9]
  • Mixture of syn- and anti-β-hydroxyallylsilanes by hydroboration of allenylsilane.[10]
  • (2S)-2-Hydroxy-4-phenylbutanenitrile by catalytic asymmetric cyanosilylation.[11]
  • Cinnamaldehyde by dehydrogenation reaction using Pd(TFA)2/4,5-diazafluorenone catalyst.[12]

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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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)
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
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)
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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