58550-78-0

Usage

Molecular Structure

1H-Indole, 3-(bromomethyl)-1-(phenylsulfonyl)consists of an indole ring with a bromomethyl group and a phenylsulfonyl group attached.

Indole Ring

A bicyclic heterocyclic compound with a seven-membered aromatic ring and a five-membered nitrogen-containing ring.

Bromomethyl Group

A halogenated alkyl group containing a bromine atom bonded to a carbon atom.

Phenylsulfonyl Group

A sulfonamide compound containing a sulfone, which is a sulfur-oxygen double bond connected to an aromatic ring.

Potential Applications

Pharmaceutical industry as a building block in the synthesis of biologically active compounds.

Use as a Reagent

In organic chemistry for the functionalization and modification of molecules.

Additional Uses

Agricultural and material science research.

Upstream product

• 58550-84-8 N-(phenylsulphonyl)-3-methylindole 
• 98-09-9 benzenesulfonyl chloride 
• 89241-33-8 1-(phenylsulfonyl)-3-(hydroxymethyl)indole 
• 83-34-1 3-Methylindole 

Downstream Products

• 130827-11-1 3-(methoxymethyl)-1-(phenylsulfonyl)-1H-indole 
• 143703-45-1 2-[1-(benzenesulfonyl)indol-3-yl]acetonitrile 
• 89241-33-8 1-(phenylsulfonyl)-3-(hydroxymethyl)indole 
• 143703-42-8 3-azidomethyl-1-benzenesulfonylindole 
• 143703-40-6 2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester 
• 143703-44-0 2-Acetylamino-2-(1-benzenesulfonyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester 
• 180964-41-4 (1-Benzenesulfonyl-1H-indol-3-ylmethylsulfanyl)-acetic acid 
• 341506-70-5 1-(phenylsulfonyl)-3-[[2-[(E)-(2,6,6-trimethyl-1-cyclohexenyl)-1-ethenyl]-1,3-dithian-2-yl]-methyl]-1H-indole 
• 1207172-97-1 C₂₄H₁₈N₂O₂S 
• 1207173-01-0 C₃₀H₂₂N₂O₄S₂ 
• 80360-20-9 1-(phenylsulfonyl)indole-3-carbaldehyde 
• 143703-43-9 diethyl <3-(1-benzenesulfonylindolyl)methyl>phosphonate 
• 143823-16-9 (1-Benzenesulfonyl-1H-indol-3-ylmethyl)-triphenyl-phosphonium; bromide 
• 4765-22-4 3-(2-amino-1-methylethyl)indole 

Relevant academic research and scientific papers

One-pot transformation of methylarenes into aromatic aldehydes under metal-free conditions

On the basis of studies of the transformation of benzylic bromides into the corresponding aromatic aldehydes by treatment with N-methylmorpholine N-oxide, various methylarenes were treated either with DBDMH in the presence of AIBN in acetonitrile at reflux (Method A) or with NBS in CCl4 under irradiation with a tungsten lamp at 30 °C (Method B), followed by treatment with N-methylmorpholine N-oxide to provide aromatic aldehydes in good yields. These methods could be adopted in one-pot transformations of methylarenes into aromatic aldehydes under conditions free of less toxic reagents and transition metals. Copyright

Direct oxidative conversion of methylarenes into aromatic nitriles

A variety of methylarenes were successfully converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with NBS or DBDMH in the presence of a catalytic amount of AIBN or BPO, followed by the reaction with molecular iodine in aq NH3 in a one-pot procedure. The present reaction is a useful and practical transition-metal-free method for the preparation of aromatic nitriles from methylarenes.

Total synthesis of lycogarubin C utilizing the Kornfeld-Boger ring contraction

An efficient synthesis of lycogarubin C (3) was completed in seven steps from the known 1-(phenylsulfonyl)indole-3-carbaldehyde in 30% overall yield, via a Diels-Alder reaction between (Z)-1,2-di(1H-indol-3-yl)ethene 9b and dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (7), followed by a Kornfeld-Boger ring contraction to form the pyrrole ring.

Unusual dimerization of N-protected bromomethylindoles/benzyl bromide with arylmetal halides: generation of indolylmethyl/benzyl radical

A detailed study on the interaction of N-protected bromomethylindoles with various types of aryl/alkyl Grignard is reported. Full experimental details on the mechanism of the unusual dimerization reaction are presented.

Unusual dimerization of N-protected bromomethylindoles using phenylmagnesium chloride

A novel dimerization of N-protected bromomethylindoles involving an exchange reaction with phenylmagnesium chloride is reported.

An efficient preparation of 1-phenylsulfonylindolyl methyl sulfoxides using KF/m-CPBA

A variety of 1-phenylsulfonylindolylmethyl sulfides are selectively oxidized to the corresponding sulfoxides using a hitherto unexplored KF/m-CPBA system. A major advantage is the absence of over-oxidation.

Regiospecific Bromination of 3-Methylindoles with NBS and Its Application to the Concise Synthesis of Optically Active Unusual Tryptophans Present in Marine Cyclic Peptides

A regiospecific bromination of substituted 3-methylindoles at either the C(3) alkyl moiety or the C(2) position was achieved via a free radical bromination or electrophilic process, respectively. The regiospecificity of the bromination could be controlled by variation of both the substituent and the N(1) protecting group on the indole ring. In addition, enantiospecific syntheses of 5-methoxytryptophan (20) and 5-hydroxy-6-chlorotryptophan (21c) as well as concise syntheses of optically active 2-bromotryptophan ethyl esters 26a,b or their substituted derivatives in three steps from bifunctional dibromoindoles were achieved via the above regiospecific process.

Regiospecific bromination of 3-methylindoles with N-bromosuccinimide

The regiospecific bromination of various substituted 3-methylindoles at either C(2) or the C(3) alkyl moiety was accomplished via an electrophilic of free radical bromination process to provide intermediates for indole alkaloid total synthesis. The regiospecificity of the bromination could be controlled by variation of both the substituent and the N(1) protecting group on the indole ring.

A Facile Synthesis of 3-Substituted Indoles

1-Benzoyl-3-bromomethylindole (2a) or 1-benzenesulfonyl-3-bromomethylindole (2b) reacts with C, N, O, and P-containing nucleophiles to give potential intermediates for the synthesis of a wide range of indole alkaloids and pharmacologically important substances, in good to excellent yields.