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Indole-5-carboxylic acid

Indole-5-carboxylic acid structure

Indole-5-carboxylic acid 

structure
  • CAS No:

    1670-81-1

  • Formula:

    C9H7NO2

  • Chemical Name:

    Indole-5-carboxylic acid

  • Synonyms:

    TIMTEC-BB SBB003951;RARECHEM AL BO 0206;5-CARBOXYINDOLE;5-INDOLECARBOXYLIC ACID;Indolecarboxylicacid,5-;INDOLE-5-CARBOXYLIC ACID;Indole-5-carboxylic acid ,98%;5-Carboxy-1H-indole

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

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.


light beige to yellow powder


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 by1H NMR and various one- and two-dimensional NMR techniques have been reported.

Indole-5-carboxylic acid Basic Attributes

161.16

161.16

124391

216-799-6

DTXSID80168218

Light beige to yellow

29339990

Characteristics

53.09000

1.86610

light beige to yellow powder

1.2480 (rough estimate)

211-213 °C (lit.)

287.44°C (rough estimate)

207.6ºC

1.5050 (estimate)

-20ºC

8.6E-08mmHg at 25°C

4.40±0.30(Predicted)

Keep in dark place,Sealed in dry,Room Temperature

Safety Information

IRRITANT

3

Xn,Xi

22-24/25-36/37/39-26

Xn

Stable under normal temperatures and pressures.

36/37/38-21/22

|Warning|H302 (14.29%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 7 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

5-indolecarboxylic acid

Indole-5-carboxylic acid Use and Manufacturing

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.


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.


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.

Computed Properties

Molecular Weight:161.16
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:161.047678466
Monoisotopic Mass:161.047678466
Topological Polar Surface Area:53.1
Heavy Atom Count:12
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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