32387-21-6

Basic information

• Product Name: 1-Methyl-1H-indole-3-carboxylic acid
• Synonyms: 1-Methylindole-3-carboxylic acid ,97%;N-Methylindole acetate;1H-Indole-3-carboxylic acid, 1-Methyl-;Methylindole-3-carboxylic;Ramosetron Impurity 7;1-METHYL-3-INDOLECARBOXYLIC ACID;1-METHYL-1H-INDOLE-3-CARBOXYLIC ACID;1-METHYLINDOLE-3-CARBOXYLIC ACID
• CAS NO: 32387-21-6
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles;Heterocycle-Indole series;Acids and Derivatives;Heterocycles;Indole
• Mol File: 32387-21-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 197-200 °C (dec.)
• Boiling Point: 389 °C at 760 mmHg
• Flash Point: 189 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.24 g/cm³
• Vapor Pressure: 9.54E-07mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.01±0.10(Predicted)
• CAS DataBase Reference: 1-Methyl-1H-indole-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-1H-indole-3-carboxylic acid(32387-21-6)
• EPA Substance Registry System: 1-Methyl-1H-indole-3-carboxylic acid(32387-21-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 32387-21-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-white solid

Uses

Reactant for preparation of bisindolyl pyrimidinones analogs of PKC inhibitor LY333531Reactant for preparation of (heteroaryl)(carboxamido)arylpyrrole derivatives as Cdc7 kinase inhibitors, antitumor and antiproliferative agentsReactant for preparation of (pyrrolidinylmethoxy)cyclohexanecarboxylic acids as antigen-4 (VLA-4) antagonistsReactant for preparation of EphB3 receptor tyrosine kinase inhibitorsReactant for preparation of pyrazolodiazepine derivatives as human P2X7 receptor antagonistsReactant for preparation of potent nonpeptidic urotensin II receptor agonistsReactant for preparation of pyrrolizidine esters, amides, and ureas as 5-HT4 receptor ligands

General Description

1-Methylindole-3-carboxylic acid is an indole derivative that can be prepared by the oxidation of 1-methylindole-3-aldehyde with alkaline potassium permanganate.

InChI:InChI=1/C10H9NO2/c1-11-6-8(10(12)13)7-4-2-3-5-9(7)11/h2-6H,1H3,(H,12,13)

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 66616-72-6 5-phenyl-1H-indole 
• 124-38-9 carbon dioxide 
• 75-91-2 tert.-butylhydroperoxide 
• 771-50-6 1H-indole-3-carboxylic acid 
• 390799-61-8 1-methylindole-3-carboxamidine E-oxime 
• 603-76-9 1-methylindole 

Downstream Products

• 1014806-01-9 N-(3-chlorophenyl)-1-methyl-1H-indole-3-carboxamide 
• 1053189-00-6 N-(2-iodophenyl)-N,1-dimethyl-1H-indole-3-carboxamide 
• 108438-43-3 methyl 1-methyl-1H-indole-3-carboxylate 
• 51206-77-0 3-(4-methoxyphenyl)-1-methyl-1H-indole 
• 154796-08-4 1-methyl-3-(4-methylphenyl)-1H-indole 
• 30020-98-5 N-methyl-3-phenylindole 
• 51206-87-2 1-methyl-3-(4-nitrophenyl)-1H-indole 
• 1175772-37-8 4-(1-methyl-1H-indol-3-yl)-benzonitrile 
• 793669-62-2 trans-4-((2S,4S)-1-{2,5-dichloro-4-[(1-methylindol-3-yl)carboxamido]phenyl}acetyl-4-methoxypyrrolidin-2-yl)methoxycyclohexane-1-carboxylic acid ethyl ester 
• 1198054-29-3 ethyl [5-chloro-2-fluoro-4-(1-methyl-3-indolylcarboxamido)phenyl]acetate 
• 1198319-97-9 (S)-(8-oxo-2-(2-phenethyl)-2,4,5,6,7,8-hexahydropyrazolo[4,3-e][1,4]diazepin-6-yl)methyl 1-methyl-1H-indole-3-carboxylate 
• 1198319-71-9 (R)-(8-oxo-2-(2-phenethyl)-2,4,5,6,7,8-hexahydropyrazolo[4,3-e][1,4]diazepin-6-yl)methyl 1-methyl-1H-indole-3-carboxylate 
• 1185863-81-3 9-methyl-1,2,3,4-tetrakis(4-trifluoromethylphenyl)-9H-carbazole 
• 1185863-79-9 1,2,3,4-tetrakis(4-tert-butylphenyl)-9-methyl-9H-carbazole 

Relevant articles and documents

Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.

Copper-catalyzed methyl esterification reactions via C-C bond cleavage

The highly effective synthesis of methyl esters from benzylic alcohols, aldehydes, or acids via copper-catalyzed C-C cleavage from tert-butyl hydroperoxide is reported in this paper for the first time. Our protocol is easily accessible and practical, making it a possible supplement for the traditional way.