10680

Anthranilic acid

puriss. p.a., ≥99.5% (T)

• Synonym(s): 2-AA, 2-Aminobenzoic acid
• Linear Formula: 2-(H₂N)C₆H₄CO₂H
• CAS Number: 118-92-3
• Molecular Weight: 137.14
• Beilstein/REAXYS Number: 471803
• EC Number: 204-287-5
• MDL number: MFCD00007712
• UNSPSC Code: 12352100
• PubChem Substance ID: 57646812
• NACRES: NA.21

Properties

• vapor density: 4.7 (vs air)
• Quality Level: 200
• grade: puriss. p.a.
• assay: ≥99.5% (T)
• form: solid
• ign. residue: ≤0.05% (as SO₄)
• mp: 144-148 °C (lit.); 145-147 °C
• anion traces: chloride (Cl^-): ≤500 mg/kg; sulfate (SO₄^2-): ≤100 mg/kg
• cation traces: Ca: ≤100 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• SMILES string: Nc1ccccc1C(O)=O
• InChI: 1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
• InChI key: RWZYAGGXGHYGMB-UHFFFAOYSA-N

Description

General description

Anthranilic acid is an ortho-substituted aniline derivative. Anthranilic acid can be obtained from carbozole via microbial transformation using Pseudomonas stutzeri. It is a substrate of enzyme anthranilate hydroxylase found in Aspergillus niger.

Application

Anthranilic acid (AA) may be employed for the following studies:

• Fluorescent labeling of glycans.
• Synthesis of triptycene and derivatives, via diazotization reaction.
• As fluorescent label for the facile labeling of oligosaccharides (acidic and neutral).
• As fluorescent label for carbohydrate analysis.
• Derivatization of oligosaccharides.
• Preparation of poly(aniline-co-o-anthranilic acid) copolymers.

Anthranilic acid has been used in the microwave-assisted preparation of 2-heptyl-3-hydroxy-4(1H)-quinolone, also called as Pseudomonas quinolone signal, which finds applications in quorum sensing mechanism.

Used for non-selective, efficient fluorescent labeling of glycans.

Other Notes

Sales restrictions may apply

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H318
• pcodes: P280 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: 302.0 °F - closed cup
• flash_point_c: 150 °C - closed cup
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves