253668-84-7

Basic information

• Product Name: 1H-Pyrrole, 2-(4-bromophenyl)-1-methyl-
• CAS NO: 253668-84-7
• Molecular Formula: C11H10BrN
• Molecular Weight: 236.111
• Mol File: 253668-84-7.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole, 2-(4-bromophenyl)-1-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 2-(4-bromophenyl)-1-methyl-(253668-84-7)
• EPA Substance Registry System: 1H-Pyrrole, 2-(4-bromophenyl)-1-methyl-(253668-84-7)

Safety Data

• Hazardous Substances Data: 253668-84-7(Hazardous Substances Data)

Upstream product

• 96-54-8 N-Methylpyrrole 
• 41931-18-4 (4-bromophenyl)hydrazine hydrochloride salt 
• 106-40-1 4-bromo-aniline 
• 57965-38-5 4-bromo-benzenediazohydroxide, sodium salt 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 1203709-75-4 4-bromo-2,4,6-trimethyldiphenyliodonium trifluoromethanesulfonate 
• 139139-81-4 bis(4-bromophenyl)iodonium triflate 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 63574-86-7 2,5-bis(4-bromophenyl)-1-methylpyrrole 

Relevant articles and documents

Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings

Polysulfide anions are endowed with unique redox properties, attracting considerable attentions for their applications in alkali metals-sulfur batteries. However, the employment of these anionic species in redox catalysis for small molecule synthesis remains underdeveloped due to their moderate-poor electrochemical potential in the ground state, whereas some of them are characterized by photoabsorptions in visible spectral regions. Herein, we disclose the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. The reaction design enables single-electron reduction of aryl halides upon the photoexcitation of tetrasulfide dianions (S42-). The resulting aryl radicals are engaged in (hetero)biaryl cross-coupling, borylation, and hydrogenation in a redox catalytic regime involving S4?-/S42- and S3?-/S32- redox couples.

Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides

Organic halides are important building blocks in synthesis, but their use in (photo)redox chemistry is limited by their low reduction potentials. Halogen-atom transfer remains the most reliable approach to exploit these substrates in radical processes despite its requirement for hazardous reagents and initiators such as tributyltin hydride. In this study, we demonstrate that a-aminoalkyl radicals, easily accessible from simple amines, promote the homolytic activation of carbon-halogen bonds with a reactivity profile mirroring that of classical tin radicals. This strategy conveniently engages alkyl and aryl halides in a wide range of redox transformations to construct sp3-sp3, sp3-sp2, and sp2-sp2 carbon-carbon bonds under mild conditions with high chemoselectivity.

Organophotocatalytic Arene Functionalization: C-C and C-B Bond Formation

Organophotocatalytic C-C and C-B bond formation reactions of aryl halides have been developed in the presence of an organophotosensitizer, 3,7-di([1,1′-biphenyl]-4-yl)-10-(4-(trifluoromethyl)phenyl)-10H-phenoxazine that has highly negative reduction potential at its photoexcited state. The developed reaction conditions are mild and allow the intermolecular C-C bond formation of the generated aryl radical with electron-rich (hetero)arenes and C-B bond formation with bis(pinacolato)diboron.