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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:
Molecular Weight:
131.13
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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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.[1] Biotransformation of 2-cyanobenzaldehyde by Euglena gracilis Z cultured photohetero-trophically has been reported.[2]

Application

2-Cyanobenzaldehyde may be used:
  • in the base-catalyzed one-pot synthesis of 3-substituted isoindolinones[3]
  • in the synthesis of 3-oxo-2,3-dihydro-1H-isoindoles, via Baylis-Hillman reaction[4]
  • in the synthesis of 3-(N-substituted amino)-1-isoindolenones[5]

Pictograms

Exclamation mark

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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    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)
    Novel synthesis of 3-(N-substituted amino)-1-isoindolenones from 2-cyanobenzaldehyde with amines.
    Sato R, et al.
    Chemistry Letters (Jpn), 9, 1599-1602 (1984)
    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
    Biotransformation of aromatic aldehydes and related compounds by Euglena gracilis Z.
    Noma Y, et al.
    Phytochemistry, 30(9), 2969-2972 (1991)

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