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I5400

Indole-5-carboxylic acid

99%

Synonym(s):

5-Carboxyindole

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About This Item

Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
1670-81-1
Molecular Weight:
161.16
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24896068
EC Number:
216-799-6
Beilstein/REAXYS Number:
124391
MDL number:
MFCD00005678
Assay:
99%
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assay

99%

mp

211-213 °C (lit.)

functional group

carboxylic acid

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

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

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.
  • 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

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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