5381-23-7

Basic information

• Product Name: 2-BROMO-3-METHYL-BENZO[B]THIOPHENE
• Synonyms: 2-BROMO-3-METHYL-BENZO[B]THIOPHENE;2-BROMO-3-METHYL-1-BENZOTHIOPHENE;2-bromo-3-methyl-benzothiophene
• CAS NO: 5381-23-7
• Molecular Formula: C9H7BrS
• Molecular Weight: 227.12088
• Mol File: 5381-23-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 114-115 °C
• Appearance: /
• Density: 1.555 g/cm3
• CAS DataBase Reference: 2-BROMO-3-METHYL-BENZO[B]THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-3-METHYL-BENZO[B]THIOPHENE(5381-23-7)
• EPA Substance Registry System: 2-BROMO-3-METHYL-BENZO[B]THIOPHENE(5381-23-7)

Safety Data

• Hazardous Substances Data: 5381-23-7(Hazardous Substances Data)

Usage

General Description

2-Bromo-3-methyl-benzo[b]thiophene is an organic compound that belongs to the class of benzo[b]thiophenes. It is a chemical with the molecular formula C9H7BrS and a molecular weight of 215.12 g/mol. 2-BROMO-3-METHYL-BENZO[B]THIOPHENE features a bromine atom and a methyl group attached to the benzo[b]thiophene ring. It is commonly used as a building block in organic synthesis and pharmaceutical research. The presence of the bromine and methyl groups make 2-bromo-3-methyl-benzo[b]thiophene a versatile intermediate in the synthesis of various pharmaceuticals, agrochemicals, and materials. It may also be used as a reagent in chemical reactions to introduce specific functional groups into organic molecules.

Upstream product

• 1455-18-1 3-methylbenzothiophene 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 3133-78-6 3-methylbenzo[b]thiophene-2-carboxylic acid 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 14282-76-9 2-bromo-3-methylthiophene 
• 3216-47-5 3-chloromethylbenzothiophene 

Downstream Products

• 3133-78-6 3-methylbenzo[b]thiophene-2-carboxylic acid 
• 82255-65-0 Benzophenanthro<3,4-d>thiophene 
• 223-47-2 anthra[2,1-d]benzo[b]thiophene 
• 40032-76-6 2-bromo-3-(bromomethyl)thiophene 

Relevant articles and documents

One-Pot Regiodirected Annulations for the Rapid Synthesis of ?-Extended Oligomers

We demonstrate the broad applicability of the annulation protocol combining, in one pot, a direct arylation and cross aldol condensation for the straightforward synthesis at gram-scale of ?-extended thiophene-based scaffolds. The regiospecific direct arylation drives the subsequent cross-aldol condensation proceed under the same basic conditions, and the overall protocol has broad applicability in the synthesis of extended aromatics wherein the thiophene ring is annulated with furans, pyridines, indoles, benzothiophenes, and benzofurans. These scaffolds can be further elaborated into ?-extended, highly fluorescent oligomers with a central deficient benzothiadiazole unit with up to nine aromatic rings through coupling reactions.

Synthetic Utility of Arylmethylsulfones: Annulative π-Extension of Aromatics and Hetero-aromatics Involving Pd(0)-Catalyzed Heck Coupling Reactions

A straightforward and general method for the synthesis of annulated thiophene, dibenzothiophene, and carbazoles analogues has been achieved involving alkylation of 2-bromo-1-(phenylsulfonylmethyl)arene/heteroarene with arylmethyl bromides/heteroarylmethyl bromides using t-BuOK as a base in DMF, followed by Pd(0)-mediated intramolecular Heck coupling in the presence of K2CO3 in DMF at 80-140 °C. The attractive feature of this protocol is that a wide variety of π-conjugated heterocycles could be readily accessed by an appropriate choice of arylmethylsulfones and benzylic bromides.

Photocatalytic Selective Bromination of Electron-Rich Aromatic Compounds Using Microporous Organic Polymers with Visible Light

Pure organic, heterogeneous, metal-free, and visible light-active photocatalysts offer a more sustainable and environmentally friendly alternative to traditional metal-based catalysts. Here we report a series of microporous organic polymers containing photoactive conjugated organic semiconductor units as heterogeneous photocatalysts for a visible-light-promoted, highly selective bromination reaction of electron-rich aromatic compounds using HBr as a bromine source and molecular oxygen as a clean oxidant. Via a simple Friedel-Crafts alkylation reaction, the microporous organic polymers were obtained by cross-linking of organic semiconductor compounds with defined valence and conduction band positions. The utilization of the simply prepared porous polymer-based photocatalytic systems opens new opportunities toward a sustainable and efficient material design for catalysis.