102547-49-9

Usage

Derivative of indole

Indole-based compound 1H-Indole, 2-(4-bromophenyl)-3-methyl- is derived from the organic compound indole, which is a bicyclic aromatic system consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Bromine attachment

4th carbon of phenyl group A bromine atom is attached to the fourth carbon of the phenyl group, which is a structural modification of the parent indole molecule, potentially affecting its chemical properties and reactivity.

Methyl group attachment

3rd carbon of indole ring A methyl group (CH3) is attached to the third carbon of the indole ring, further modifying the structure and properties of the compound.

Aromatic and heterocyclic properties

Characteristic features The compound exhibits aromatic and heterocyclic properties due to the presence of the benzene and pyrrole rings in its structure, which contribute to its stability and chemical behavior.

Applications in synthesis

Pharmaceutical, agrochemical, and dye industries 1H-Indole, 2-(4-bromophenyl)-3-methylis commonly used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and dyes, taking advantage of its aromatic and heterocyclic nature.

Potential bioactivity

Medicinal chemistry applications The compound shows potential bioactivity, meaning it may interact with biological systems, and is being studied for its possible use in medicinal chemistry, potentially leading to the development of new drugs or therapies.

Important intermediate

Preparation of complex organic molecules Due to its structural features, 1H-Indole, 2-(4-bromophenyl)-3-methylis an important intermediate in the preparation of various complex organic molecules, making it a valuable building block in organic synthesis.

Upstream product

• 10342-83-3 4'-Bromopropiophenone 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 1433772-22-5 N'-(1-(2-aminophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 
• 1122-91-4 4-bromo-benzaldehyde 
• 551-93-9 2-aminoacetophenone 

Relevant academic research and scientific papers

Synthesis of indolo[2,1-: A] isoquinoline derivatives via visible-light-induced radical cascade cyclization reactions

We describe a photocatalyzed transformation for the synthesis of the indolo[2,1-a]isoquinoline core structure. This redox neutral reaction features mild reaction conditions and exceptional functional group tolerance. A series of valuable indolo[2,1-a]isoquinoline derivatives bearing various functional groups were synthesized using this method in good to excellent yields.

Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions

A direct alkoxycarbonylation/cyclization reaction is accomplished under visible light-induced photoredox catalysis. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in good to excellent yields. It is worth noting that this method not only can afford the synthesis of indolo[2,1-a]isoquinolines but also can provide an alternative route for generating complex target structures bearing carboxylic esters.

Electrochemical Tri- and Difluoromethylation-Triggered Cyclization Accompanied by the Oxidative Cleavage of Indole Derivatives

Considering their unique roles in organic synthesis, and pharmaceutical and agrochemical applications, the development of fluoroalkylation, cyclization, and indole oxidative cleavage are important topics. Herein, an unprecedented electrochemical tri- and difluoromethylation/cyclization/indole oxidative cleavage process occurring in an undivided cell is presented. The protocol employs a readily prepared Langlois reagent as the fluoroalkyl source, affording a series of tri- or difluoromethylated 2-(2-acetylphenyl)isoquinoline-1,3-diones in good yields with excellent stereoselectivity. It is worth noting that this new methodology merges the fluoroalkylation/cyclization of N-substituted acrylamide alkenes with the oxidative cleavage of an indole C(2)=C(3) bond under external oxidant-free conditions.

Manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides

A simple and practical method for the synthesis of phosphoryl-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and benzimidazo[2,1-a]isoquinolin-6(5H)-ones through manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles or 2-arylbenzimidazoles with disubstituted phosphine oxides was developed. In this transformation, new C-P bond and C-C bond were constructed simultaneously under silver-free conditions, exhibiting a broad substrate scope. It was noted that not only diarylphosphine oxides but also dialkyl and arylalkyl-phosphine oxides were compatible with the conditions. This journal is

Base-promoted domino reaction for the synthesis of 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes

A base-promoted domino reaction to synthesize the 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes has been developed. This strategy provides a simple and beneficial way for the construction of 2,3-disubstituted indole compounds from readily available starting materials under mild conditions.

Efficient construction of fused indolines with a 2-quaternary center via an intramolecular heck reaction with a low catalyst loading

An efficient construction of fused indolines with a 2-quaternary center through a palladium-catalyzed intramolecular Heck reaction of N-(2(2-halobenzoxyl)-2,3-disubstituted indoles is disclosed. This protocol provided a straightforward access to diverse fused indolines with good functional group tolerance.