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A9628

Sigma-Aldrich

2-Aminobenzaldehyde

≥98%

Synonym(s):

2-Formylaniline, Anthranilaldehyde, o-Aminobenzaldehyde

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About This Item

Empirical Formula (Hill Notation):
C7H7NO
CAS Number:
529-23-7
Molecular Weight:
121.14
EC Number:
208-454-3
MDL number:
MFCD00007709
UNSPSC Code:
12352100
PubChem Substance ID:
57653901
NACRES:
NA.22

Quality Level

200

assay

≥98%

form

powder

shipped in

dry ice

storage temp.

−20°C

SMILES string

Nc1ccccc1C=O

InChI

1S/C7H7NO/c8-7-4-2-1-3-6(7)5-9/h1-5H,8H2

InChI key

FXWFZIRWWNPPOV-UHFFFAOYSA-N

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Application

Reactant for:
  • Preparation of quinoline derivatives as antiviral agents
  • Preparation of electroluminescent materials for OLEDs
  • Friedlander-type synthesis
  • Preparation of 2-tosylaminophenyl cyclopropylmethanols for gold-catalyzed cyclopropyl carbinol rearrangement
  • Benzyl C-H bond amination of arylmethylamines catalyzed by hydroxy-TEMPO
  • Silver-catalyzed aniline mediated cascade hydroamination/cycloaddition reactions

Caution

Polymerizes rapidly at room temperature. May yield slightly hazy solution in ethanol due to the presence of a small amount of polymer.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

235.4 °F

flash_point_c

113 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Moamen S Refat et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 70(1), 234-242 (2007-09-04)
The, nitrin, 2-aminobenzaldehyde phenylhydrazone (2ABPH) was synthesis by refluxing 2-nitrobenzaldehyde with phenylhydrazine in ethanolic solvent. Three transition metal (II) complexes of 2ABPH have been prepared. Elemental analysis, molar conductivity, IR, UV, 1H NMR, and mass spectra, as well as TG/DTG
Yi-Feng Wang et al.
Chemistry, an Asian journal, 4(12), 1834-1838 (2009-10-16)
Generally, amine-catalyzed enantioselective transformations rely on chiral enamine or unsaturated iminium intermediates. Herein, we report a protocol involving dual activation by an aromatic iminium and hydrogen-bonding. An enantioselective aza-Michael-Henry domino reaction of 2-aminobenzaldehydes with nitroolefins has been developed through this
H R Kim et al.
Analytical biochemistry, 223(2), 205-207 (1994-12-01)
We developed an assay system for ornithine aminotransferase (EC 2.6.1.13) using ninhydrin. Pyrroline 5-carboxylate, a product of enzymatic transamination, reacts with ninhydrin under hot acidic conditions to form a reddish pigment soluble in ethanol. The millimolar extinction coefficient of reaction
Riccardo Montioli et al.
The FEBS journal, 286(14), 2787-2798 (2019-04-09)
Among the over 50 gyrate atrophy-causing mutations of ornithine δ-aminotransferase (OAT), the R180T involves an active site residue located at the dimer interface, which in the crystal structure of OAT complexed with 5-fluoromethylornithine engages a salt bridge with the α-carboxylate
Riccardo Montioli et al.
Biochimica et biophysica acta. Molecular basis of disease, 1864(11), 3629-3638 (2018-09-27)
Gyrate atrophy (GA) is a rare recessive disorder characterized by progressive blindness, chorioretinal degeneration and systemic hyperornithinemia. GA is caused by point mutations in the gene encoding ornithine δ-aminotransferase (OAT), a tetrameric pyridoxal 5'-phosphate-dependent enzyme catalysing the transamination of l-ornithine
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