59050-41-8

Basic information

• Product Name: 1-METHYL-2-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID
• Synonyms: 1H-Indole-3-carboxylic acid, 1-methyl-2-phenyl-
• CAS NO: 59050-41-8
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.28
• Mol File: 59050-41-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 456.449°C at 760 mmHg
• Flash Point: 229.852°C
• Appearance: /
• Density: 1.202g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: 1-METHYL-2-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-2-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID(59050-41-8)
• EPA Substance Registry System: 1-METHYL-2-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID(59050-41-8)

Safety Data

• Hazardous Substances Data: 59050-41-8(Hazardous Substances Data)

Usage

Derivative of indole

The compound is derived from the indole structure, which is a bicyclic aromatic organic compound that is a building block for many natural and synthetic compounds.

Carboxylic acid functional group

The presence of a carboxylic acid group (-COOH) in the compound contributes to its chemical reactivity and potential applications in the synthesis of other organic compounds.

Potential building block for pharmaceuticals

1-METHYL-2-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID can be used as a starting material for the synthesis of various pharmaceuticals due to its unique chemical structure.

Medicinal properties

The compound has been studied for its potential as an anti-inflammatory and anti-cancer agent, indicating its possible use in the development of new drugs for the treatment of inflammation and cancer.

Applications in material development

The compound may have potential applications in the development of new materials, possibly due to its unique chemical structure and reactivity.

Precursor for synthesis of other organic compounds

1-METHYL-2-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID can serve as a precursor for the synthesis of other organic compounds, further expanding its potential applications in various fields.

InChI:InChI=1/C16H13NO2/c1-17-13-10-6-5-9-12(13)14(16(18)19)15(17)11-7-3-2-4-8-11/h2-10H,1H3,(H,18,19)

Upstream product

• 62-53-3 aniline 
• 35401-49-1 (Z)-methyl 3-phenyl-3-(phenylamino)propenoate 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 36779-17-6 methyl 2-phenyl-1H-indole-3-carboxylate 
• 108-86-1 bromobenzene 
• 32387-21-6 1-methyl-3-indolecarboxylic acid 
• 773875-08-4 methyl 1-methyl-2-phenyl-1H-indole-3-carboxylate 
• 3558-24-5 1-methyl-2-phenyl-1H-indole 
• 124-38-9 carbon dioxide 
• 773137-52-3 ethyl 1-methyl-2-phenyl-1H-indole-3-carboxylate 
• 87613-34-1 1-methyl-2-phenyl-1H-indole-3-carbonitrile 

Downstream Products

• 26821-93-2 (1-methyl-2-phenyl-1H-indol-3-yl)(phenyl)methanone 
• 1160172-07-5 ethyl 4-(1-methyl-2-phenyl-1H-indole-3-yl)benzoate 
• 1160172-08-6 3-(4-biphenyl)-1-methyl-2-phenyl-1H-indole 
• 1160172-06-4 1-methyl-2-phenyl-3-(4-(trifluoromethyl)phenyl)-1H-indole 

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.

Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides

The Lewis acid-mediated carboxylation of arenes with CO2 has been successfully applied to 1-substituted indoles and pyrroles by using dialkylaluminum chlorides instead of aluminum trihalides. Thus, the carboxylation of 1-methylindoles, 1-benzyl-, and 1-phenylpyrroles proceeds regioselectively with the aid of an equimolar amount of Me2AlCl under CO2 pressure (3.0 MPa) at room temperature to afford the corresponding indole-3-carboxylic acids and pyrrole-2-carboxylic acids in 61-85% yields, while the same treatment of 1,2,5-trimethylpyrrole affords the 3-carboxylic acid in 52% yield.

Photocarboxylation in the Presence of Aromatic Amines and Carbon Dioxide

Phenylethylenes (1), biphenyl, and 1-methyl-2-phenylindole underwent carboxylation upon photolysis in the presence of aromatic amines (2) and carbon dioxide.