53541-90-5

Basic information

• Product Name: 3-(4-methylbenzyl)-1H-indole
• Synonyms: 3-(4-methylbenzyl)-1H-indole
• CAS NO: 53541-90-5
• Molecular Weight: 221.302
• Mol File: 53541-90-5.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 3-(4-methylbenzyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methylbenzyl)-1H-indole(53541-90-5)
• EPA Substance Registry System: 3-(4-methylbenzyl)-1H-indole(53541-90-5)

Safety Data

• Hazardous Substances Data: 53541-90-5(Hazardous Substances Data)

Upstream product

• 120-72-9 indole 
• 104-82-5 4-Methylbenzyl chloride 
• 589-18-4 4-Methylbenzyl alcohol 
• 5339-85-5 2-aminophenethyl alcohol 
• 496-15-1 1-indoline 
• 487-89-8 Indole-3-carboxaldehyde 
• 89980-67-6 p-methylbenzylmagnesium bromide 
• 944686-02-6 (1H-indol-3-yl)(p-tolyl)methanol 
• 459-56-3 4-fluorobenzylic alcohol 
• 104-81-4 4-Methylbenzyl bromide 
• 15121-84-3 2-nitro-benzeneethanol 

Relevant articles and documents

Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).

Nickel-catalyzed C3-alkylation of indoles with alcohols: Via a borrowing hydrogen strategy

An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcohols as the alkylating reagents has been developed. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcohols and substituted indoles. Mechanistic studies suggested that the reaction proceeds through a borrowing hydrogen pathway.

Manganese-Catalyzed Regioselective Dehydrogenative C-versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation

The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air-and moisture-stable manganese catalyst provides access to either C3-or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen autotransfer strategy.