537684-22-3

Basic information

• Product Name: 2-(2-METHYLPHENYL)-1H-INDOLE
• Synonyms: 1H-INDOLE, 2-(2-METHYLPHENYL)-;2-(2-METHYLPHENYL)-1H-INDOLE;2-O-TOLYL-1H-INDOLE
• CAS NO: 537684-22-3
• Molecular Formula: C₁₅H₁₃N
• Molecular Weight: 207.275
• Mol File: 537684-22-3.mol
• Article Data: 36

Chemical Properties

• Melting Point: 92-93 °C(Solv: ethanol (64-17-5))
• Boiling Point: 382.4±11.0 °C(Predicted)
• Appearance: /
• Density: 1.129±0.06 g/cm3(Predicted)
• PKA: 16.75±0.30(Predicted)
• CAS DataBase Reference: 2-(2-METHYLPHENYL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-METHYLPHENYL)-1H-INDOLE(537684-22-3)
• EPA Substance Registry System: 2-(2-METHYLPHENYL)-1H-INDOLE(537684-22-3)

Safety Data

• Hazardous Substances Data: 537684-22-3(Hazardous Substances Data)

Usage

Description

2-(2-METHYLPHENYL)-1H-INDOLE, also known as 2-methyl-2-phenylindole, is a heterocyclic chemical compound belonging to the indole class of organic compounds. It features a five-membered nitrogen-containing ring fused to a benzene ring, making it a valuable intermediate in the synthesis of various biologically active compounds.
Used in Pharmaceutical Industry:
2-(2-METHYLPHENYL)-1H-INDOLE is used as a building block for the production of pharmaceutical drugs due to its unique structure and properties that facilitate the synthesis of diverse compounds with potential therapeutic applications.
Used in Agrochemical Industry:
2-(2-METHYLPHENYL)-1H-INDOLE is used in the synthesis of biologically active compounds for agrochemical applications, contributing to the development of new products for crop protection and other agricultural uses.
It is crucial to handle and use 2-(2-METHYLPHENYL)-1H-INDOLE with caution, adhering to proper safety guidelines and regulations to ensure safe and effective utilization in its respective industries.

Upstream product

• 120-72-9 indole 
• 13165-77-0 toluenesulfinic acid 
• 133-59-5 Toluene-2-sulfonyl chloride 
• 95-46-5 2-methylphenyl bromide 
• 100-63-0 phenylhydrazine 
• 577-16-2 2-Methylacetophenone 
• 933-88-0 ortho-toluoyl chloride 
• 22978-49-0 2-methyl-N-(2-methylphenyl)benzamide 
• 3469-06-5 benzocyclobutenone 
• 221044-05-9 N-(2-pyrimidyl)indole 
• 62-53-3 aniline 
• 178910-14-0 2-phenylamino-1-o-tolyl-ethanone 
• 615-37-2 ortho-methylphenyl iodide 
• 36268-59-4 N-(2-(cyanomethyl)phenyl)acetamide 

Downstream Products

• 947402-59-7 N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole 
• 1392423-09-4 1-methyl-6-phenyl-11H-benzo[a]carbazole 
• 18595-87-4 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one 
• 304479-23-0 N-(2-cyanophenyl)-2-methylbenzamide 

Relevant articles and documents

Divergent Coupling of Benzocyclobutenones with Indoles via C?H and C?C Activations

Highly selective divergent coupling reactions of benzocyclobutenones and indoles, in which the chemoselectivity is controlled by catalysts, are reported herein. The substrates undergo C2(indole)–C8(benzocyclobutenone) coupling to produce benzylated indoles and benzo[b]carbazoles in the Ni- and Ru-catalyzed reactions. A completely different selectivity pattern C2(indole)–C2(benzocyclobutenone) coupling to form arylated indoles is observed in the Rh-catalyzed reaction. Preliminary mechanistic studies suggest C?H and C?C activations in the reaction pathway. Synthetic utility of this protocol is demonstrated by the selective synthesis of three different types of carbazoles from the representative products.

An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives

We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is

Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics

Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.