29981-98-4

Basic information

• Product Name: 1H-Pyrrolo[1,2-a]benzimidazole,2,3-dihydro-3-methyl-(9CI)
• Synonyms: 1H-Pyrrolo[1,2-a]benzimidazole,2,3-dihydro-3-methyl-(9CI)
• CAS NO: 29981-98-4
• Molecular Formula: C11H12N2
• Molecular Weight: 172.22638
• Product Categories: BENZIMIDAZOLE
• Mol File: 29981-98-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrrolo[1,2-a]benzimidazole,2,3-dihydro-3-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[1,2-a]benzimidazole,2,3-dihydro-3-methyl-(9CI)(29981-98-4)
• EPA Substance Registry System: 1H-Pyrrolo[1,2-a]benzimidazole,2,3-dihydro-3-methyl-(9CI)(29981-98-4)

Safety Data

• Hazardous Substances Data: 29981-98-4(Hazardous Substances Data)

Upstream product

• 108413-26-9 1-(but-3-en-1-yl)-1H-benzo[d]imidazole 
• 150649-19-7 2-(1-methylcyclopropyl)-1H-benzimidazole 
• 54624-57-6 2-bromo-1H-1,3-benzodiazole 
• 134856-55-6 N-(but-3-enyl)-2-nitrobenzenamine 
• 88-73-3 2-Chloronitrobenzene 
• 51-17-2 benzoimidazole 
• 201230-82-2 carbon monoxide 
• 134856-38-5 N-(3-buten-1-yl)-1,2-phenylenediamine 

Relevant articles and documents

Switchable Regioselective 6-endo or 5-exo Radical Cyclization via Photoredox Catalysis

Controlling the regioselectivity of radical cyclizations to favor the 6-endo mode over its kinetically preferred 5-exo counterpart is difficult without introducing substrate prefunctionalization. To address this challenge, we have developed a simple method for reagent controlled regioselective radical cyclization of halogenated N-heterocycles onto pendant olefins. Radical generation occurs under mild photoredox conditions with control of the regioselectivity governed by the rate of hydrogen atom transfer (HAT). Utilizing a polarity-matched thiol-based HAT agent promotes the highly selective formation of the 5-exo cyclization product. Conversely, limiting the solubility of the HAT reagent Hantzsch ester (HEH) leads to selective formation of the thermodynamically favored 6-endo product. This occurs through an initial 5-exo cyclization, with the resulting alkyl radical intermediate undergoing neophyl rearrangement to form the 6-endo product. Development of this switchable catalysis strategy allows for two modes of divergent reactivity to form either the 6-endo or 5-exo product, generating fused N-heteroaromatic/saturated ring systems.

Enantioselective Ni-Al Bimetallic Catalyzed exo -Selective C-H Cyclization of Imidazoles with Alkenes

A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.

Microwave-assisted C-H bond activation: A rapid entry into functionalized heterocycles

(Matrix presented) Microwave irradiation strongly accelerates the rhodium-catalyzed intramolecular coupling of a benzimidazole C-H bond to pendant alkenes. The cyclic products were formed in moderate to excellent yields with reaction times less than 20 min. Additionally, the use of microwave irradiation allowed the reactions to be performed without any solvent purification and with minimal precautions to exclude air.