Methyl indole-3-carboxylate

Base Information

• Chemical Name: Methyl indole-3-carboxylate
• CAS No.: 942-24-5
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29339900
• Mol file: 942-24-5.mol

Synonyms:Indole-3-carboxylicacid, methyl ester (6CI,7CI,8CI);3-Carbomethoxyindole;3-Methoxycarbonylindole;Methyl 1H-indole-3-carboxylate;Methylindole-3-carboxylate;Methyl indolyl-3-carboxylate;

Chemical Property of Methyl indole-3-carboxylate

Chemical Property:

• Appearance/Colour: light brown amorphous powder
• Vapor Pressure: 0.000153mmHg at 25°C
• Melting Point: 149-152 °C
• Refractive Index: 1.639
• Boiling Point: 331.7 °C at 760 mmHg
• PKA: 15.42±0.30(Predicted)
• Flash Point: 154.4 °C
• PSA: 42.09000
• Density: 1.253 g/cm³
• LogP: 1.95450
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble methanol and dimethyl sulfoxide. Insoluble in water.

Purity/Quality:

99% ^*data from raw suppliers

Methyl indole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl indole-3-carboxylate is a reagent in the preaparation of oncrasin-1 derivatives which is a novel inhibitor of the C-terminal domain of RNA polymerase II. Reactant for preparation of:Nitric oxide synthase (nNOS) inhibitorSProtein kinase c alpha (PKCα) inhibitorsInhibitors of the C-terminal domain of RNA polymerase II as antitumor agentsKinase insert domain receptor (KDR) inhibitorsOrganocatalysts for the anti-Mannich reactionVery late antigen-4 (VLA-4) antagonistsInhibitors of Human 5-LipoxygenaseSerotonin 5-HT4 receptor antagonistsHyaluronidase inhibitorsReactant for:Enantioselective Meerwein-Eschenmoser Claisen rearrangement reactions?

Technology Process of Methyl indole-3-carboxylate

There total 8 articles about Methyl indole-3-carboxylate 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: 77.0%

N-benzenesulfonyl-1H-indole-3-carboxylic acid methyl ester (116325-17-8) → 5-benzenesulfonyl-1H-indole-3-carboxylic acid methyl ester + 7-benzenesulfonyl-1H-indole-3-carboxylic acid methyl ester + 3-methoxycarbonylindole (942-24-5)

Guidance literature:

With triethylamine; In acetonitrile; for 1h; Irradiation;

DOI:10.1016/j.tet.2007.01.064

Reference yield: 56.0%

ethyl acetate (141-78-6) + methyl 1-tert-butoxycarbonyl-1H-indole-3-carboxylate (338760-26-2) → 3-methoxycarbonylindole (942-24-5) + tert-butyl 3-(3-ethoxy-3-oxopropanoyl)-1H-indole-1-carboxylate (1383532-74-8) + ethyl acetoacetate (141-97-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -40 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.04.008

Reference yield: 39.0%

tert.-butylhydroperoxide (75-91-2) + 1H-indole-3-carboxylic acid (771-50-6) → 1-methyl-3-indolecarboxylic acid (32387-21-6) + 3-methoxycarbonylindole (942-24-5) + methyl 1-methyl-1H-indole-3-carboxylate (108438-43-3)

Guidance literature:

With copper quinolate; In water; dimethyl sulfoxide; at 120 ℃; for 24h;

DOI:10.1021/jo4016387

upstream raw materials:

methyl 1-phenyl-1H-1,2,3-triazole-5-carboxylate

methyl 1H-indole-1-carboxylate

methyl 1-phenyl-1H-1,2,3-triazole-4-carboxylate

3-hydroxy-2-methylene-3-(2-nitrophenyl)propanoic acid methyl ester

Downstream raw materials:

6H,13H-pyrazino<1,2-a:4,5-a'>diindole-6,13-dione

methyl 2-(2-cyanophenyl)acetate

methyl 7-iodoindole-3-carboxylate

methyl 5-iodo-1H-indole-3-carboxylate

Refernces

• 1、 Zhu, Yan,Yan, Hong,Lu, Linhua,Liu, Defu,Rong, Guangwei,Mao, Jincheng. "Copper-catalyzed methyl esterification reactions via C-C bond cleavage". . p. 9898 - 9905. Retrieved 2013/10/22.
• 2、 Hong, Xuechuan,France, Stefan,Padwa, Albert. "A dipolar cycloaddition approach toward the kopsifoline alkaloid framework". . p. 5962 - 5976. Retrieved 2008/02/07.