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N10802

Sigma-Aldrich

2-Nitrobenzaldehyde

98%

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Synonym(s):
o-NBA, ortho-nitrobenzaldehyde
Linear Formula:
O2NC6H4CHO
CAS Number:
552-89-6
Molecular Weight:
151.12
Beilstein:
742624
EC Number:
209-025-3
MDL number:
MFCD00007132
UNSPSC Code:
12352100
PubChem Substance ID:
24897457
NACRES:
NA.22

Quality Level

200

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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335,H412

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Studies on some Schiff base complexes of CoII, NiII and CuII derived from salicylaldehyde and o-nitrobenzaldehyde.
Zaki Z M, et al.
Spectroscopy Letters, 31(4), 757-766 (1998)
Verónica Leyva et al.
Physical chemistry chemical physics : PCCP, 13(32), 14685-14693 (2011-07-08)
Ab initio surface-hopping dynamics calculations have been performed to simulate the intramolecular excited state hydrogen transfer dynamics of ortho-nitrobenzaldehyde (o-NBA) in the gas phase from the electronic S(1) excited state. Upon UV excitation, the hydrogen is transferred from the aldehyde
Thierry Delatour et al.
Journal of agricultural and food chemistry, 51(22), 6371-6379 (2003-10-16)
A convenient method is presented for the preparation of the carbon-13-labeled 2-nitrobenzaldehyde derivatives of the nitrofuran metabolites 3-amino-2-oxazolidinone (AOZ), semicarbazide (SC), 1-aminohydantoin (AH), and 3-amino-5-morpholinomethyl-2-oxazolidinone (AMOZ), with the purpose of using them as internal standards for the quantification of trace
An-Hu Li et al.
Organic & biomolecular chemistry, 5(1), 61-64 (2006-12-14)
A highly effective one-pot Friedländer quinoline synthesis using inexpensive reagents has been developed. o-Nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of catalytic HCl (aq.) and subsequently condensed in situ with aldehydes or ketones to form mono- or
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