B1334

Sigma-Aldrich

Benzaldehyde

ReagentPlus®, ≥99%

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:

Quality Level

vapor density

3.7 (vs air)

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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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.

Packaging

1, 3 kg in glass bottle
18 kg in steel drum
2, 5, 100 g in glass bottle

Quality

Chlorine-free

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1990 9 / PGIII

WGK Germany

WGK 1

Flash Point(F)

145.4 °F

Flash Point(C)

63 °C

N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines.
Alanthadka A and Maheswari CU.
Advanced Synthesis & Catalysis, 357(6), 1199-1203 (2015)
Experimental and theoretical studies on the hydrogen-bond-promoted enantioselective hetero-Diels-alder reaction of Danishefsky's diene with benzaldehyde.
Zhang X, et al.
The Journal of Organic Chemistry, 71(7), 2862-2869 (2006)
Hydrogenation of benzaldehyde over palladium intercalated bentonite catalysts: Kinetic studies.
Divakar D, et al.
Catalysis Letters, 125(3-4), 277-282 (2008)
Activation of Mg-Al hydrotalcite catalysts for aldol condensation reactions.
Rao KK, et al.
J. Catal., 173(1), 115-121 (1998)
Benzaldehyde hydrogenation over supported nickel catalysts.
Saadi A, et al.
J. Mol. Catal. A: Chem., 253(1), 79-85 (2006)
Articles
The aldol condensation reaction is an organic reaction introduced by Charles Wurtz, who first prepared the β-hydroxy aldehyde from acetaldehdye in 1872.
Read More
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.
Read More

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