Indole-5-carboxylic acid

Base Information

• Chemical Name: Indole-5-carboxylic acid
• CAS No.: 1670-81-1
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29339990
• European Community (EC) Number: 216-799-6
• DSSTox Substance ID: DTXSID80168218
• Nikkaji Number: J195.309E
• Wikidata: Q27455355
• Metabolomics Workbench ID: 87110
• ChEMBL ID: CHEMBL2018158
• Mol file: 1670-81-1.mol

Synonyms:5-indolecarboxylic acid;indole-5-carboxylic acid

Chemical Property of Indole-5-carboxylic acid

Chemical Property:

• Appearance/Colour: light beige to yellow powder
• Vapor Pressure: 8.6E-08mmHg at 25°C
• Melting Point: 211-213 °C(lit.)
• Refractive Index: 1.5050 (estimate)
• Boiling Point: 419.6 °C at 760 mmHg
• PKA: 4.40±0.30(Predicted)
• Flash Point: 207.6 °C
• PSA: 53.09000
• Density: 1.408 g/cm³
• LogP: 1.86610
• Storage Temp.: −20°C
• Solubility.: Soluble in ethanol (50 mg/ml), dimethyl sulfoxide and methanol.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 161.047678466
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Indole-5-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-21/22
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2)C=C1C(=O)O
• Uses: 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.

Technology Process of Indole-5-carboxylic acid

There total 18 articles about Indole-5-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

5-methoxycarbonylindole (1011-65-0) → 1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 90h;

DOI:10.1021/acs.jmedchem.5b00585

Reference yield: 92.0%

5-bromo-1H-indole (10075-50-0) + formyl acetic anhydride (2258-42-6) → 1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0)

Guidance literature:

5-bromo-1H-indole; formyl acetic anhydride; With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80 - 90 ℃; for 2.5h; Inert atmosphere;

With hydrogenchloride; In water; pH=Ca. 4 - 6;

DOI:10.1080/00397911.2010.528851

Reference yield: 83.0%

5-methyl-1H-indole (614-96-0) → 1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0)

Guidance literature:

With dipotassium peroxodisulfate; oxygen; CrH₆Mo₆O₂₄^(3-)*3H₃N*3H⁽¹⁺⁾; In water; at 50 ℃; for 24h; under 760.051 Torr; Green chemistry;

DOI:10.1039/d1dt01967h

upstream raw materials:

1H-indole-5-carbonitrile

indole-3,5-dicarboxylic acid

3,5-diacetylindole

5-bromo-2-indolecarboxylic acid

Downstream raw materials:

1H-indole-5-carboxylic acid benzyl ester

5-methoxycarbonylindole

1H-Indole-5-carboxylic acid

3-formylindole-5-carboxylic acid

Refernces

• 1、 Ghosh, Arun K.,Raghavaiah, Jakka,Shahabi, Dana,Yadav, Monika,Anson, Brandon J.,Lendy, Emma K.,Hattori, Shin-Ichiro,Higashi-Kuwata, Nobuyo,Mitsuya, Hiroaki,Mesecar, Andrew D.. "Indole Chloropyridinyl Ester-Derived SARS-CoV-2 3CLpro Inhibitors: Enzyme Inhibition, Antiviral Efficacy, Structure-Activity Relationship, and X-ray Structural Studies". supporting information. p. 14702 - 14714. Retrieved 2021/10/01.
• 2、 Banerjee, Srirupa,Chatterjee, Debnath,Paul, Abhijit,Yadav, Somnath. "Synthesis of 3-alkenylindoles through regioselective C-H alkenylation of indoles by a ruthenium nanocatalyst". supporting information. p. 140 - 148. Retrieved 2020/03/27.