143952-53-8

Basic information

• Product Name: 1H-Indole-1-carboxylic acid, 2-methyl-, methyl ester
• Synonyms: 1H-Indole-1-carboxylic acid, 2-methyl-, methyl ester
• CAS NO: 143952-53-8
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Mol File: 143952-53-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole-1-carboxylic acid, 2-methyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-1-carboxylic acid, 2-methyl-, methyl ester(143952-53-8)
• EPA Substance Registry System: 1H-Indole-1-carboxylic acid, 2-methyl-, methyl ester(143952-53-8)

Safety Data

• Hazardous Substances Data: 143952-53-8(Hazardous Substances Data)

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 616-38-6 carbonic acid dimethyl ester 
• 911022-62-3 N-(methoxycarbonyl)-2'-vinylacetanilide 
• 911022-76-9 methyl (1-methylethenyl)(2-vinylphenyl)carbamate 
• 52562-18-2 2-(prop-1-en-1-yl)aniline 
• 1501966-66-0 methyl N-[2-(3-iodoprop-1-yn-1-yl)phenyl]carbamate 
• 1184039-97-1 methyl N-[2-(3-hydroxyprop-1-yn-1-yl)phenyl]carbamate 
• 23206-21-5 methyl 2-vinylaniline-N-carboxylate 
• 79-22-1 methyl chloroformate 
• 3867-18-3 2-vinylaniline 

Downstream Products

• 144137-01-9 (1-methoxycarbonylindol-2-yl)methyl(triphenyl)phosphonium bromide 
• 29475-88-5 trans-2-styrylindole 

Relevant articles and documents

Palladium-catalyzed diastereoselective oxyarylation of 2-alkylindoles

Diastereoselective oxyarylation of N-protected 2-alkylindoles with commercially available boronic acids and TEMPO as a mild oxidant to give N-protected 2-aryl-2-alkyl-3-(2-chloroacetoxy)indolines is described. Reactions are easy to conduct, and product indolines containing a fully substituted C-center are obtained in good yields with good to excellent selectivities.

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles

The dimethyltitanocene methylenation of N-acylamides derived from ortho-vinylanilines, ortho-allylaniline, and ortho-vinylbenzylamine provides the corresponding enamides, which upon exposure to the second generation Grubbs ruthenium catalyst give access to indoles, 1,4-dihydroquinolines, and 1,2-dihydroisoquinolines, respectively. This sequential protocol also allows the synthesis of dihydrobenzoazepines, although the ring-closing metathesis (RCM) step is complicated by the alkene isomerization processes. From certain substrates, the direct annulation is observed in the titanium-mediated step, which is likely to occur through an olefin metathesis-intramolecular olefination sequence.