Indole-2-carboxylic acid

Base Information

• Chemical Name: Indole-2-carboxylic acid
• CAS No.: 1477-50-5
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29339990
• European Community (EC) Number: 216-030-4
• NSC Number: 16598
• DSSTox Substance ID: DTXSID20163782
• Nikkaji Number: J132E
• Wikipedia: Indole-2-carboxylic acid
• Wikidata: Q27461367
• Pharos Ligand ID: 3R2K8ACC8Y7J
• Metabolomics Workbench ID: 38110
• ChEMBL ID: CHEMBL278390
• Mol file: 1477-50-5.mol

Synonyms:indole-2-carboxylic acid

Chemical Property of Indole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: Off-white crystal powder
• Vapor Pressure: 8.6E-08mmHg at 25°C
• Melting Point: 202-206 °C(lit.)
• Refractive Index: 1.5050 (estimate)
• Boiling Point: 419.6 °C at 760 mmHg
• PKA: 4.44±0.30(Predicted)
• Flash Point: 207.6 °C
• PSA: 53.09000
• Density: 1.408 g/cm³
• LogP: 1.86610
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in clear yellow solution 5% in ethanol, dimethyl sulfoxi
• XLogP3: 2.3
• 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:

98% ^*data from raw suppliers

Indole-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)C(=O)O
• Uses: ? ;Reactant for total synthesis of (±)-dibromophakellin and analogs1? ;Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine2? ;Reactant for stereoselective preparation of renieramycin G analogs3? ;Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization4? ;Reactant for Pd-catalyzed cyclization5? ;Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis( Reactant for total synthesis of (±)-dibromophakellin and analogs, synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine, stereo selective preparation of renieramycin G analogs, preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization, Pd-catalyzed cyclization and N,N?-(pentane)diylbis[indolecarboxamide] and N,N?-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives.

Technology Process of Indole-2-carboxylic acid

There total 93 articles about Indole-2-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: 99.9%

2-carbethoxyindole (3770-50-1,117770-52-2) → Indole-2-carboxylic acid (1477-50-5,1228050-17-6)

Guidance literature:

With potassium hydroxide; In water; at 120 ℃; for 0.5h;

Reference yield: 98.0%

1-(phenylsulfonyl)-1H-indole-2-carboxylic acid (40899-93-2) → Indole-2-carboxylic acid (1477-50-5,1228050-17-6)

Guidance literature:

With sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1055/s-0029-1219918

Reference yield: 96.0%

o-nitrophenylpyruvic acid (5461-32-5) → Indole-2-carboxylic acid (1477-50-5,1228050-17-6)

Guidance literature:

With sodium dithionite; In 1,4-dioxane; water; for 3h; Reflux;

DOI:10.1016/j.tetlet.2018.09.039

upstream raw materials:

indole

2-methyl-1H-indole

1-acetyl-2-methylindole

1,2,3,4-tetrahydrocarbazole

Downstream raw materials:

indole-2-carboxylic acid methyl ester

2-carbethoxyindole

3-(3-phenyl-propyl)-indole

3-acetylindole

Refernces

• 1、 Tokala, Ramya,Sana, Sravani,Lakshmi, Uppu Jaya,Sankarana, Prasanthi,Sigalapalli, Dilep Kumar,Gadewal, Nikhil,Kode, Jyoti,Shankaraiah, Nagula. "Design and synthesis of thiadiazolo-carboxamide bridged β-carboline-indole hybrids: DNA intercalative topo-IIα inhibition with promising antiproliferative activity". . . Retrieved 2020/10/27.
• 2、 Su, Chenliang,Yu, Kunyi,Zhang, Hanjie,Zhu, Yongfa. "Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions". supporting information. p. 1956 - 1960. Retrieved 2020/04/10.