227960-12-5

Basic information

• Product Name: 5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER;5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER;METHYL 5-METHYL-1H-INDOLE-3-CARBOXYLATE;RARECHEM AL BF 0707;Methyl 5-methylindole-3-carboxylate;1H-Indole-3-carboxylicacid,5-Methyl-,Methylester
• CAS NO: 227960-12-5
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Product Categories: Indole
• Mol File: 227960-12-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 345.1°Cat760mmHg
• Flash Point: 162.5°C
• Appearance: /
• Density: 1.212g/cm³
• Vapor Pressure: 6.28E-05mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 15.59±0.30(Predicted)
• CAS DataBase Reference: 5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER(227960-12-5)
• EPA Substance Registry System: 5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER(227960-12-5)

Safety Data

• Hazardous Substances Data: 227960-12-5(Hazardous Substances Data)

Usage

General Description

5-Methylindole-3-carboxylic acid methyl ester is a chemical compound with the molecular formula C11H11NO2. It is a methyl ester derivative of 5-methylindole-3-carboxylic acid, which is an important intermediate in the synthesis of pharmaceuticals and organic compounds. This chemical is commonly used as a building block in the production of various drugs and bioactive compounds. It is also utilized in research and development processes for the creation of new drugs and functional materials. 5-Methylindole-3-carboxylic acid methyl ester has potential applications in the pharmaceutical and chemical industries due to its versatile and valuable chemical properties.

InChI:InChI=1/C11H11NO2/c1-7-3-4-10-8(5-7)9(6-12-10)11(13)14-2/h3-6,12H,1-2H3

Upstream product

• 623-10-9 N-(4-methylphenyl)hydroxylamine 
• 922-67-8 propynoic acid methyl ester 
• 227959-99-1 methyl 1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxylate 

Downstream Products

• 10242-02-1 5-methyl-1H-indole-3-carboxylic acid 
• 1377936-23-6 3-(4-{[1-(3,4-Dimethyl-benzyl)-5-methyl-1H-indole-3-carbonyl]-amino}-benzylamino)-propionic acid 
• 1377936-42-9 1-(3,4-dimethylbenzyl)-N-(4-formylphenyl)-5-methyl-1H-indole-3-carboxamide 
• 1377936-39-4 1-(3,4-dimethylbenzyl)-N[4-(hydroxymethyl)phenyl]-5-methyl-1H-indole-3-carboxamide 
• 1377936-32-7 4-(5-(1-(3,4-dimethylbenzyl)-5-methyl-1H-indol-3-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde 
• 1377936-30-5 (4-(5-(1-(3,4-dimethylbenzyl)-5-methyl-1H-indol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol 
• 1377936-27-0 1-(3,4-dimethylbenzyl)-5-methyl-1H-indole-3-carboxylic acid 
• 1377935-90-4 1-(4-{5-[1-(3,4-dimethylbenzyl)-5-methyl-1H-indol-3-yl]-1,2,4-oxadiazol-3-yl}benzyl)azetidine-3-carboxylic acid 
• 1377936-25-8 methyl 1-(3,4-dimethylbenzyl)-5-methyl-1H-indole-3-carboxylate 

Relevant articles and documents

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Aryliminopropadienone-C-Amidoketenimine-Amidinoketene-2-Aminoquinolone Cascades and the Ynamine-Isocyanate Reaction

Imidoylketenes 11 and oxoketenimines 12 are generated by flash vacuum thermolysis of Meldrum's acid derivatives 9, pyrrolediones 17 and 18, and triazole 19 and are observed by IR spectroscopy. Ketenimine-3-carboxylic acid esters 12a are isolable at room temperature. Ketenes 11 and ketenimines 12 undergo rapid interconversion in the gas phase, and the ketenes cyclize to 4-quinolones 13. When using an amine leaving group in Meldrum's acid derivatives 9c, the major reaction products are aryliminopropadienones, ArN=C=C=C=O (15). The latter react with 1 equiv of nucleophile to produce ketenimines 12 and with 2 equiv to afford malonic acid imide derivatives 16. N-Arylketenimine-C-carboxamides 12c cyclize to quinolones 13c via the transient amidinoketenes 11c at temperatures of 25-40 °C. This implies rapid interconversion of ketenes and ketenimines by a 1,3-shift of the dimethylamino group, even at room temperature. This interconversion explains previously poorly understood outcomes of the ynamine-isocyanate reaction. The solvent dependence of the tautomerism of 4-quinolones/4-quinolinols is discussed. Rotational barriers of NMe2 groups in amidoketenimines 12c and malonioc amides and amidines 16 (24) are reported.