Indole-4-carboxylic acid

Base Information

• Chemical Name: Indole-4-carboxylic acid
• CAS No.: 2124-55-2
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29339900
• Mol file: 2124-55-2.mol

Synonyms:1H-indole-4-carboxylate;1H-indole-4-carboxylic acid;

Chemical Property of Indole-4-carboxylic acid

Chemical Property:

• Appearance/Colour: Beige powder
• Vapor Pressure: 8.6E-08mmHg at 25°C
• Melting Point: 213-214 °C(lit.)
• Boiling Point: 419.6 °C at 760 mmHg
• PKA: 3.90±0.10(Predicted)
• Flash Point: 207.6 °C
• PSA: 53.09000
• Density: 1.408 g/cm³
• LogP: 1.86610
• Storage Temp.: Keep Cold

Purity/Quality:

99% ^*data from raw suppliers

Indole-4-Carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Reactant for preparation of substituted indole derivatives as histamine H3 antagonistsReactant for preparation of potent and selective inhibitors of human reticulocyte 15-lipoxygenase-1Reactant for preparation of inhibitors of Gli1-mediated transcription in Hedgehog pathwayReactant for preparation of pyridinyl carboxylates as SARS-CoV 3CL proinhibitorsReactant for preparation of substituted bipiperidinylmethyl amides as CCR3 membrane binding ligandsReactant for preparation of indole amide hydroxamic acids as potent inhibitors of histone deacetylasesReactant for preparation of 2-[[[4′-chloro-[1,1-biphenyl]-4-yl]thio]methyl]-N-hydroxybutanamide derivatives as specific metalloproteinase

Technology Process of Indole-4-carboxylic acid

There total 7 articles about Indole-4-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%

methyl 1H-indole-4-carboxylate (39830-66-5) → 1H-indole-4-carboxylic acid (2124-55-2)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2010.08.103

Reference yield: 80.0%

4-bromo-1H-indole (52488-36-5) + formyl acetic anhydride (2258-42-6) → 1H-indole-4-carboxylic acid (2124-55-2)

Guidance literature:

4-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 4h; Inert atmosphere;

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

DOI:10.1080/00397911.2010.528851

Reference yield:

4-cyanoindole (16136-52-0) → 1H-indole-4-carboxylic acid (2124-55-2)

Guidance literature:

With potassium hydroxide;

upstream raw materials:

4-cyanoindole

6-chloro-2-nitrotoluene

4-chloro-1H-indole-2-carboxylic acid

(2-chloro-6-nitro-phenyl)-pyruvic acid

Downstream raw materials:

benzyl indole-4-carboxylate

ethyl indole-4-carboxylate

1-methyl-1H-indole-4-carboxylic acid methyl ester

2,3-dihydro-1H-indole-4-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、 Gadakh, Amol V.,Chikanna, Dinesh,Rindhe, Sahebrao S.,Karale, Bhausaheb K.. "Heteroaryl hydroxycarbonylation: An efficient, robust, practically scalable approach using formyl acetate as the co source". experimental part. p. 658 - 666. Retrieved 2011/12/16.