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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000365511
0000365511
0000340202
0000340169
0000256165

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Michael C Haibach et al.
Journal of the American Chemical Society, 133(7), 2100-2103 (2011-02-02)
Aminobenzaldehydes react with indoles in an unprecedented cascade reaction. This acid-catalyzed redox-neutral annulation proceeds via a condensation/1,5-hydride shift/ring-closure sequence. Polycyclic azepinoindoles and related compounds are obtained in a single step with good to excellent yields.
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
Shoko Yamazaki et al.
The Journal of organic chemistry, 75(4), 1188-1196 (2010-01-30)
Quinolines are an important class of compounds, and the development of new efficient synthetic strategies for the construction of quinolines is of considerable interest. Zinc triflate catalyzed cyclization of ethenetricarboxylate derivatives with 2-aminobenzaldehydes has been examined. The reaction of ethenetricarboxylate
Sarah C Atkinson et al.
Structure (London, England : 1993), 26(7), 948-959 (2018-05-29)
Protein dynamics manifested through structural flexibility play a central role in the function of biological molecules. Here we explore the substrate-mediated change in protein flexibility of an antibiotic target enzyme, Clostridium botulinum dihydrodipicolinate synthase. We demonstrate that the substrate, pyruvate
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