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HomeProduct name listIndole-5-carboxylic acid

Indole-5-carboxylic acid

Synonym(s):5-Carboxyindole

  • CAS NO.:1670-81-1
  • Empirical Formula: C9H7NO2
  • Molecular Weight: 161.16
  • MDL number: MFCD00005678
  • EINECS: 216-799-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-06-04 15:29:52
Indole-5-carboxylic acid Structural

What is Indole-5-carboxylic acid?

Chemical properties

light beige to yellow powder

The Uses of Indole-5-carboxylic acid

Indole-5-carboxylic acid is the suitable reagent used to study the intermolecular 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. Also used as reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles, as potential anticancer immunomodulators, synthesis of indirubin derivatives and amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway.

The Uses of Indole-5-carboxylic acid

Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles, as potential anticancer immunomodulators 1 Reactant for preparation of indolyl-quinolines via metal- and solvent-free autoxidative coupling reaction 2 Reactant for preparation of anthranilic acids using bromamine-B oxidant and palladium chloride catalyst 3 Reactant for synthesis of indirubin derivatives 4 Reactant for preparation of amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway 5 Reactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesity.

The Uses of Indole-5-carboxylic acid

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.

Definition

ChEBI: Indole-5-carboxylic acid is an indolecarboxylic acid in which the carboxy group is the only substituent and is located at position 5. It has a role as a plant metabolite.

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.

Properties of Indole-5-carboxylic acid

Melting point: 211-213 °C (lit.)
Boiling point: 287.44°C (rough estimate)
Density  1.2480 (rough estimate)
refractive index  1.5050 (estimate)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  Soluble in ethanol (50 mg/ml), dimethyl sulfoxide and methanol.
pka 4.40±0.30(Predicted)
form  Powder
color  Light beige to yellow
BRN  124391
CAS DataBase Reference 1670-81-1(CAS DataBase Reference)

Safety information for Indole-5-carboxylic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Indole-5-carboxylic acid

InChIKey IENZCGNHSIMFJE-UHFFFAOYSA-N

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