10680

Anthranilsäure

≥99.5% (T), solid, puriss. p.a.

• Synonym(e): 2-AA, 2-Amino-benzoesäure
• Lineare Formel: 2-(H₂N)C₆H₄CO₂H
• CAS-Nummer: 118-92-3
• Molekulargewicht: 137.14
• NACRES: NA.21
• PubChem Substance ID: 57646812
• UNSPSC Code: 12352100
• EC Number: 204-287-5
• MDL number: MFCD00007712
• Beilstein/REAXYS Number: 471803
• Assay: ≥99.5% (T)
• Form: solid

Eigenschaften

• Produktname: Anthranilsäure, puriss. p.a., ≥99.5% (T)
• vapor density: 4.7 (vs air)
• Quality Segment: 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
• functional group: carboxylic acid
• 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

Beschreibung

General description

Anthranilic acid is an ortho-substituted aniline derivative.[1] 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.[1]
• Synthesis of triptycene and derivatives, via diazotization reaction.
• As fluorescent label for the facile labeling of oligosaccharides (acidic and neutral).[2]
• As fluorescent label for carbohydrate analysis.[2]
• Derivatization of oligosaccharides.[2]
• 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.

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Sicherheitshinweise

• pictograms: GHS05
• signalword: Danger
• hcodes: H318
• pcodes: P280 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1
• Lagerklasse: 11 - Combustible Solids
• wgk: 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