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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

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

Certificates of Analysis (COA)

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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
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
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
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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