172877-90-6

Basic information

• Product Name: 1-[2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one
• Synonyms: 1-[2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one
• CAS NO: 172877-90-6
• Molecular Weight: 406.3
• Mol File: 172877-90-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-[2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one(172877-90-6)
• EPA Substance Registry System: 1-[2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one(172877-90-6)

Safety Data

• Hazardous Substances Data: 172877-90-6(Hazardous Substances Data)

Upstream product

• 172877-89-3 1-[2-methyl-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one 
• 80360-21-0 1-(benzenesulfonyl)-2-methyl-1H-indole 
• 85678-41-7 N-benzenesulphonyl-2-methyl-3-thiophenoxyindole 
• 4106-18-7 1-(phenylsulfonyl)-1H-benzo[d][1,2,3]triazole 
• 95-20-5 2-methyl-1H-indole 

Downstream Products

• 1597408-43-9 (E)-1-[2-(2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one 
• 1597408-46-2 (E)-1-[2-(4,5-dimethoxy-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one 
• 1558054-04-8 (E)-1-[2-(4-chloro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]-propan-1-one 
• 1559070-28-8 (E)-1-[2-(4-fluoro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]-propan-1-one 
• 1597408-48-4 (E)-1-[2-(4,5-dichloro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one 
• 1597408-49-5 (E)-2-bromo-1-[2-(2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]-propan-1-one 
• 1597408-54-2 (E)-2-bromo-1-[2-(4-chloro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one 
• 1597408-55-3 (E)-2-bromo-1-[2-(4-fluoro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one 
• 1597408-57-5 (E)-2-bromo-1-[2-(4,5-dichloro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one 
• 1597408-58-6 (E)-1-[2-(2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]-2-(phenylsulfonyl)propan-1-one 
• 1597408-61-1 (E)-1-[2-(4,5-dimethoxy-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]-2-(phenylsulfonyl)propan-1-one 
• 1597408-62-2 (E)-1-[2-(4-chloro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]-2-(phenylsulfonyl)propan-1-one 
• 1597408-65-5 (E)-1-[2-(4-fluoro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]-2-(phenylsulfonyl)propan-1-one 
• 1589574-37-7 (E)-1-[2-(4,5-dichloro-2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl]-2-(phenylsulfonyl)propan-1-one 

Relevant articles and documents

Total synthesis of calothrixin B and its analogs

The total synthesis of calothrixin B and its analogs was achieved starting from 2-methylindole. The synthesis involved an electrocyclization of 2-nitroarylvinyl-3-phenylsulfonylvinylindoles as a key step to give 2-nitroaryl-4-methoxy-3-methylcarbazoles. Oxidation of these compounds followed by reductive cyclization led to N-phenylsulfonylquinocarbazoles. These quinocarbazoles underwent hydrolysis and aerial oxidation in one pot to give the target compounds. A linear synthesis of calothrixin B and its analogs has been established from commercially available 2-methylindole. The thermal electrocyclization of 2-nitroarylvinyl-3-phenylsulfonylindole was a key step in the synthesis. The synthesis of calothrixin B and its analogs was achieved in 12-22 % overall yield over twelve steps. Copyright

Synthesis and cycloaddition of 2,4-dihydropyrroloindoles

Friedel-Crafts acylation of 2-methyl-1-phenylsulfonylindole 6 gave the 3-acyl derivatives 7 which upon side chain bromination with N-bromosuccinimide (NBS) followed by treatment with primary amines afforded the title compounds 9.Diels-Alder reaction of 9 with dimethyl acetylenedicarboxylate (DMAD) gave the polysubstituted carbazoles 12.