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B1334

Sigma-Aldrich

Benzaldehyde

ReagentPlus®, ≥99%

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Synonym(s):
Bitter almond
Linear Formula:
C6H5CHO
CAS Number:
Molecular Weight:
106.12
Beilstein/REAXYS Number:
471223
EC Number:
MDL number:
eCl@ss:
39023701
PubChem Substance ID:

vapor density

3.7 (vs air)

Quality Level

vapor pressure

4 mmHg ( 45 °C)

product line

ReagentPlus®

assay

≥99%

form

liquid

autoignition temp.

374 °F

expl. lim.

1.4 %, 20 °F

refractive index

n20/D 1.545 (lit.)

pH

5.9 (20 °C)

bp

178-179 °C (lit.)

mp

−26 °C (lit.)

density

1.044 g/cm3 at 20 °C (lit.)

SMILES string

O=Cc1ccccc1

InChI

1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H

InChI key

HUMNYLRZRPPJDN-UHFFFAOYSA-N

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1 of 4

This Item
41809912010W212717
vibrant-m

B1334

Benzaldehyde

vibrant-m

418099

Benzaldehyde

vibrant-m

12010

Benzaldehyde

vibrant-m

W212717

Benzaldehyde

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

400

refractive index

n20/D 1.545 (lit.)

refractive index

n20/D 1.545 (lit.)

refractive index

n20/D 1.545 (lit.)

refractive index

n20/D 1.545 (lit.)

form

liquid

form

liquid

form

liquid

form

liquid

bp

178-179 °C (lit.)

bp

178-179 °C (lit.)

bp

178-179 °C (lit.)

bp

178-179 °C (lit.)

mp

−26 °C (lit.)

mp

−26 °C (lit.)

mp

−26 °C (lit.)

mp

−26 °C (lit.)

General description

Benzaldehyde is an aromatic aldehyde. Rotational transitions in benzaldehyde have been explained based on its microwave absorption spectrum. The conversion of benzaldehyde into reduced compounds in the presence of metal oxides has been studied. SmFeO3 (perovskite-type oxide catalyst) catalyzed cyanosilylation reaction of benzaldehyde with trimethylsilyl cyanide (TMSCN) has been reported.

Application

Benzaldehyde has been used as a standard in the quantification of Achillea ligustica essential oil by GC-MS (Gas Chromatography-Mass Spectrometry).
Benzaldehyde may be used in the following studies:
  • Preparation of optically active 1-phenylpropan-1-ol.
  • Synthesis of meso-tetraphenylporphins and chlorins.
  • As a test compound to study oxidative amidation reaction of aliphatic primary/secondary amines using N-heterocyclic carbine as a catalyst.
  • Synthesis of 2-phenyl-2,3-dihydro-4H-pyran-4-one with high enantioselectivity by hetero-Diels-Alder (HDA) reaction with Danishefsky′s diene.

Quality

Chlorine-free

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 1

flash_point_f

145.4 °F

flash_point_c

63 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Reduction of benzaldehyde on metal oxides.
Haffad D, et al.
J. Catal., 172(1), 85-92 (1997)
Cyanosilylation of benzaldehyde with TMSCN over perovskite-type oxide catalyst prepared by thermal decomposition of heteronuclear cyano complex precursors.
Yamaguchi S, et al.
Research on Chemical Intermediates, 41(12), 9551-9560 (2015)
Gas phase hydrogenation of benzaldehyde over supported copper catalysts. Effect of copper loading.
Lanasri K, et al.
Studies in Surface Science and Catalysis, 174, 1279-1282 (2008)
B Rosche et al.
Applied microbiology and biotechnology, 57(3), 309-315 (2002-01-05)
Extracts of 14 filamentous fungi were examined regarding their potential for production of (R)-phenylacetylcarbinol [(R)-PAC], which is the chiral precursor in the manufacture of the pharmaceuticals ephedrine and pseudoephedrine. Benzaldehyde and pyruvate were transformed at a scale of 1.2 ml
Microwave Spectrum of Benzaldehyde.
Kakar RK, et al.
J. Chem. Phys. , 52(7), 3803-3813 (1970)

Articles

The aldol condensation reaction is an organic reaction introduced by Charles Wurtz, who first prepared the β-hydroxy aldehyde from acetaldehdye in 1872.

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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