349089
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
98%
Quality Level
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
signalword
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
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
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 349089-5G | 04061826767009 |
| 349089-1G | 04061826766941 |