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N10802

Sigma-Aldrich

2-Nitrobenzaldehyde

98%

Synonym(s):

o-NBA, ortho-nitrobenzaldehyde

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About This Item

Linear Formula:
O2NC6H4CHO
CAS Number:
552-89-6
Molecular Weight:
151.12
Beilstein/REAXYS Number:
742624
EC Number:
209-025-3
MDL number:
MFCD00007132
UNSPSC Code:
12352100
PubChem Substance ID:
24897457
NACRES:
NA.22

assay

98%

form

crystals

bp

153 °C/23 mmHg (lit.)

mp

42-44 °C (lit.)

SMILES string

[O-][N+](=O)c1ccccc1C=O

InChI

1S/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H

InChI key

CMWKITSNTDAEDT-UHFFFAOYSA-N

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General description

The 2-Nitrobenzyl group of 2-nitrobenzaldehyde is photolabile that can be cleaved when exposed to UV-light.

Application

2-Nitrobenzaldehyde can react with chitosan to form 2-nitrobenzyl-chitosan, which is soluble in trifluoroacetic acid and can also be electrospun into nanofiber matrices. On photolysis, the nitrobenzyl group is cleaved to form neat chitosan nanofiber matrices. The same principle has been applied for the preparation of gelatin nanofiber matrices. The condensation of o-NBA with 2-aminobenzothiazole forms o-nitrobenzylidene 2-aminobenzothiazole, a Schiff′s base that can react with metal ions to form complexes.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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Gelatin nanofiber matrices derived from schiff base derivative for tissue engineering applications.
Jaiswal D, et al.
Journal of Biomedical Nanotechnology, 11(11), 2067-2080 (2015)
Two-photon photolysis of 2-nitrobenzaldehyde monitored by fluorescent-labeled nanocapsules.
Diaspro A, et al.
The Journal of Physical Chemistry B, 107(40), 11008-11012 (2003)
A smart methodology to fabricate electrospun chitosan nanofiber matrices for regenerative engineering applications.
Nada A A, et al.
Polymers For Advanced Technologies, 25(5), 507-515 (2014)
S Laimgruber et al.
Physical chemistry chemical physics : PCCP, 10(26), 3872-3882 (2008-08-09)
The first intermediate of the photochemical transformation of ortho-nitrobenzaldehyde to ortho-nitrosobenzoic acid in acetonitrile solvent has been characterized by femtosecond spectroscopy and time-dependent density functional theory (TDDFT) calculations. Femtosecond stimulated Raman spectroscopy (FSRS) indicates that this intermediate adopts a ketene
Annapaola Migani et al.
Chemical communications (Cambridge, England), 47(22), 6383-6385 (2011-05-10)
o-Nitrobenzaldehyde is photolabile because of an irreversible phototautomerization, whereas comparable aromatic compounds function as photoprotectors because the tautomerization is reversible. In this experimental and theoretical study we track down the cause of this difference to the electronic changes that occur
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