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349089

Sigma-Aldrich

2-Cyanobenzaldehyde

98%

Synonym(s):

2-Formylbenzonitrile, Phthalaldehydonitrile (8CI), o-Cyanobenzaldehyde, o-Formylbenzonitrile

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About This Item

Linear Formula:
NCC6H4CHO
CAS Number:
7468-67-9
Molecular Weight:
131.13
MDL number:
MFCD00017503
UNSPSC Code:
12352100
PubChem Substance ID:
24861495
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

103-105 °C (lit.)

functional group

aldehyde
nitrile

SMILES string

O=Cc1ccccc1C#N

InChI

1S/C8H5NO/c9-5-7-3-1-2-4-8(7)6-10/h1-4,6H

InChI key

QVTPWONEVZJCCS-UHFFFAOYSA-N

General description

Aldol addition of enolizable 1,3-dicarbonyl compounds to 2-cyanobenzaldehyde in the presence of a tertiary amine has been reported. Biotransformation of 2-cyanobenzaldehyde by Euglena gracilis Z cultured photohetero-trophically has been reported.

Application

2-Cyanobenzaldehyde may be used:
  • in the base-catalyzed one-pot synthesis of 3-substituted isoindolinones
  • in the synthesis of 3-oxo-2,3-dihydro-1H-isoindoles, via Baylis-Hillman reaction
  • in the synthesis of 3-(N-substituted amino)-1-isoindolenones

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ6297
STBG3770V
STBF6744V
STBF1834V
STBD7558V

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Application of baylis-hillman methodology in a new synthesis of 3-oxo-2, 3-dihydro-1H-isoindoles.
Song YS, et al.
Journal of Heterocyclic Chemistry, 40(5), 939-942 (2003)
The aldol addition of readily enolizable 1, 3-dicarbonyl compounds to 2-cyanobenzaldehyde in the synthesis of novel 3-substituted isoindolinones.
More V, et al.
Synthesis, 2011(18), 3027-3031 (2011)
Biotransformation of aromatic aldehydes and related compounds by Euglena gracilis Z.
Noma Y, et al.
Phytochemistry, 30(9), 2969-2972 (1991)
Antonia Di Mola et al.
Beilstein journal of organic chemistry, 11, 2591-2599 (2016-01-07)
New bifunctional chiral ammonium salts were investigated in an asymmetric cascade synthesis of a key building block for a variety of biologically relevant isoindolinones. With this chiral compound in hand, the development of further transformations allowed for the synthesis of
Marcus Angelin et al.
The Journal of organic chemistry, 75(17), 5882-5887 (2010-08-10)
The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analogue synthesis
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