Indole-3-carboxylic acid

Base Information

• Chemical Name: Indole-3-carboxylic acid
• CAS No.: 771-50-6
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29339900
• European Community (EC) Number: 212-231-6
• UNII: 59711R38B0
• DSSTox Substance ID: DTXSID50227886
• Nikkaji Number: J113.034J
• Wikidata: Q27103090
• Metabolomics Workbench ID: 38287
• ChEMBL ID: CHEMBL387527
• Mol file: 771-50-6.mol

Synonyms:3-carboxyindole;indole-3-carboxylic acid

Chemical Property of Indole-3-carboxylic acid

Chemical Property:

• Appearance/Colour: light beige powder
• Vapor Pressure: 8.6E-08mmHg at 25°C
• Melting Point: 232-240 °C
• Refractive Index: 1.5050 (estimate)
• 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.: 2-8°C
• Solubility.: Soluble in 95% Ethanol: 50 mg/ml, also soluble in methanol.
• XLogP3: 2
• 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-3-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

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C(=O)O

Technology Process of Indole-3-carboxylic acid

There total 65 articles about Indole-3-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: 98.0%

1-benzylindole-3-carboxylic acid (27018-76-4) → 1H-indole-3-carboxylic acid (771-50-6)

Guidance literature:

With aluminum (III) chloride; In benzene; at -10 - 20 ℃; for 18h;

DOI:10.1016/j.tet.2015.12.028

Reference yield: 96.0%

3-methoxycarbonylindole (942-24-5) → 1H-indole-3-carboxylic acid (771-50-6)

Guidance literature:

With iodine; aluminium; In acetonitrile; at 80 ℃; for 18h;

DOI:10.1021/acs.joc.1c00034

Reference yield: 95.0%

indole (120-72-9) + carbon dioxide (124-38-9,18923-20-1) → 1H-indole-3-carboxylic acid (771-50-6)

Guidance literature:

With lithium tert-butoxide; In N,N-dimethyl-formamide; at 100 ℃; for 24h; under 760.051 Torr; Reagent/catalyst; Time;

DOI:10.3987/COM-14-S(K)94

upstream raw materials:

indole

3-Methylindole

3-cyano-1H-indole

indole-3-carbinol

Downstream raw materials:

Indole-3-carbonyl chloride

anthranilic acid

1H,1H'-2,2'-Biindolylidene-3,3'-dione

methyl 1-methyl-1H-indole-3-carboxylate

Refernces

• 1、 Abdel-Aziz, Hatem A.,Abdulla, maha,Abo-Ashour, mahmoud f.,Ahmad, Rehan,Al-Khayal, Khayal,Al-Rashood, Sara T.,Al-Warhi, Tarfah,Alharbi, Amal,Ayyad, Rezk R.,El-Haggar, Radwan,Eldehna, Wagdy m.. "Development of 2-oindolin-3-ylidene-indole-3-carbohydrazide derivatives as novel apoptotic and anti-proliferative agents towards colorectal cancer cells". . p. 319 - 328. Retrieved 2020/12/23.
• 2、 Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan. "Cleavage of Carboxylic Esters by Aluminum and Iodine". . p. 4254 - 4261. Retrieved 2021/03/09.