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A9628

Sigma-Aldrich

2-Aminobenzaldehyde

≥98%

Sinónimos:

2-Formylaniline, Anthranilaldehyde, o-Aminobenzaldehyde

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About This Item

Fórmula empírica (notación de Hill):
C7H7NO
Número de CAS:
529-23-7
Peso molecular:
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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000365511
0000365511
0000340202
0000340169
0000256165

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P Spiteller et al.
Phytochemistry, 57(3), 361-363 (2001-06-08)
Feeding experiments with 13C- and fluorine-labelled precursors were performed to reveal the biosynthesis of 2-aminobenzaldehyde in flowers of Robinia pseudoacacia and Philadelphus coronarius. The results are in agreement with the transformation of anthranilic acid to indole followed by oxidative ring
Nitin T Patil et al.
The Journal of organic chemistry, 77(14), 6179-6185 (2012-07-12)
DFT computational studies in the cyclization of aminoalkyne (see structure), which is generated in situ by 2-aminobenzaldehydes and terminal alkynes in the presence of metals and secondary amines, has been investigated. The study revealed that the mode of cyclization (exo
Hsien-Po Chiu et al.
Chembiochem : a European journal of chemical biology, 13(3), 364-366 (2012-01-10)
Sticky residue: Pyrroline-carboxy-lysine (Pcl) can be readily incorporated into proteins expressed in E. coli and mammalian cells by using the pyrrolysyl tRNA/tRNA synthetase pair. Pcl can be used as a single amino acid purification tag and can be site-specifically modified
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
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.
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