I5400

Indole-5-carboxylic acid

99%

• Synonym(s): 5-Carboxyindole
• Empirical Formula (Hill Notation): C₉H₇NO₂
• CAS Number: 1670-81-1
• Molecular Weight: 161.16
• Beilstein/REAXYS Number: 124391
• EC Number: 216-799-6
• MDL number: MFCD00005678
• UNSPSC Code: 12352100
• PubChem Substance ID: 24896068
• NACRES: NA.22

Properties

• assay: 99%
• mp: 211-213 °C (lit.)
• SMILES string: OC(=O)c1ccc2[nH]ccc2c1
• InChI: 1S/C9H7NO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10H,(H,11,12)
• InChI key: IENZCGNHSIMFJE-UHFFFAOYSA-N

Description

General description

Indole-5-carboxylic acid is an indole derivative. On electropolymerization, it affords electroactive polymer film of poly(indole-5-carboxylic-acid). Different concentrations of indole-5-carboxylic acid in sulfuric acid solution has been investigated for the preventive action against mild steel corrosion. On electropolymerization it affords a trimeric product. Characterization studies of the trimeric product by ¹H NMR and various one- and two-dimensional NMR techniques have been reported.

Application

• Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles, as potential anticancer immunomodulators
• Reactant for preparation of indolyl-quinolines via metal- and solvent-free autoxidative coupling reaction
• Reactant for preparation of anthranilic acids using bromamine-B oxidant and palladium chloride catalyst
• Reactant for synthesis of indirubin derivatives
• Reactant for preparation of amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway
• Reactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesity

Indole-5-carboxylic acid is the suitable reagent used to study the intramolecular excited state proton transfer in indole-2-carboxylic acid and indole-5-carboxylic acid in various solvents in acidic, basic, and neutral media by steady state and time resolved fluorescence spectroscopy. It may be used in the electrochemical synthesis of poly(indole-5-carboxylic acid) (PICA) films.

Safety Information

• Storage Class: 13 - Non Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)