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Usage

Uses

Used in Academic Research:
3-Bromo-N-(p-toluenesulfonyl)indole is used as a research chemical for the synthesis and study of various organic compounds. It aids in understanding the chemical properties and reactivity of indole-based structures, which is crucial for the development of new chemical methodologies and applications.
Used in Industrial Research:
In the industrial sector, 3-Bromo-N-(p-toluenesulfonyl)indole is used as a key intermediate in the synthesis of pharmaceuticals and other chemical products. Its unique structure and reactivity make it a valuable component in the development of new drugs and materials with potential therapeutic or commercial applications.
Used in Pharmaceutical Production:
3-Bromo-N-(p-toluenesulfonyl)indole is used as a building block in the production of various pharmaceuticals. Its presence in the molecular structure can influence the biological activity and pharmacological properties of the final drug product, making it an essential component in the development of new medications.

Upstream product

• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 98-59-9 p-toluenesulfonyl chloride 
• 120-72-9 indole 
• 26690-80-2 2-(N-tert-butoxycarbonylamino)ethanol 
• 370090-66-7 1-tosyl-1H-indole-3-carboxylic acid 
• 1484-27-1 3-bromoindole 

Downstream Products

• 151451-40-0 ethyl (E)-3-[1-(4-toluenesulfonyl)indole-3-yl]propenoate 
• 333303-40-5 3-bromo-4-N-p-toluenesulfonylindole 
• 314083-22-2 3-(1-piperazyl)-1-tosylindole 
• 1322744-52-4 (S)-2-benzyloxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester 
• 887339-08-4 1-tosyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)-1H-indole 
• 887338-43-4 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1H-indole 
• 1352714-47-6 2-(3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)-1H-indol-1-yl)acetic acid 
• 1352714-46-5 C₄₆H₄₇NO₇ 
• 1621087-22-6 C₂₁H₁₉NO₅S 
• 115920-44-0 carbazomycin G 
• 1257657-39-8 2-allyl-1-(toluene-4-sulfonyl)-1H-indole 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 763138-83-6 1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 

Relevant academic research and scientific papers

Syntheses of Heterocycle-2,3-Fused Indoline and Azaindoline -Derivatives

We describe a practical method for synthesizing heterocycle-2,3-fused indoline or azaindoline derivatives through haloetherification and cyclization. We applied this method in syntheses of six- to eight-membered heterocycle-2,3-fused indoline and azaindoline derivatives. These derivatives, which contain sp 3 -hybridized carbons, might be useful as new scaffolds in medicinal chemistry.

Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons

A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).

Cooperativity within the catalyst: alkoxyamide as a catalyst for bromocyclization and bromination of (hetero)aromatics

Alkoxyamide has been reported as a catalyst for the activation ofN-bromosuccinimide to perform bromocyclization and bromination of a wide range of substrates in a lipophilic solvent, where adequate suppression of the background reactions was observed. The key feature of the active site is the alkoxy group attached to the sulfonamide moiety, which facilitates the acceptance as well as the delivery of bromonium species from the bromine source to the substrates.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles

A novel indole-2,3-epoxide equivalent, 2-hydroxyindoline-3-triethylammonium bromide, was found to be a convenient reagent for formal C3-electrophilic reactions of indoles with various nucleophiles. By taking advantage of the nucleophilic character of the

Synthesis of 2-arylindoles by Suzuki coupling reaction of 3-bromoindoles with hindered benzoboronic acids

A new synthetic method for 2-arylindoles has been developed, the process through Suzuki coupling reaction of 3-bromoindoles with hindered boronic acid catalyzed by Pd(OAc)2/PCy3, and a series of 2-arylindoles have been synthesized in moderate to high yields.

A quick, mild and efficient bromination using a CFBSA/KBr system

Bromination is a fundamental transformation in organic chemistry and brominated compounds as building blocks are of paramount importance in organic synthesis. In our study, we have developed an efficient method of bromination by using a CFBSA/KBr system at room temperature in a short reaction time. Notably, this approach has been proven to be applicable to a range of substrates including 1,3-diketones and β-keto esters, phenols, aromatic amines and heteroarenes with good to excellent yields.

A practical lewis base catalyzed electrophilic chlorination of arenes and heterocycles

A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chemistry. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.

Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin

Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions.