69445-55-2

Basic information

• Product Name: 1H-Benzimidazole, 6-methoxy-1-phenyl-
• CAS NO: 69445-55-2
• Molecular Formula: C14H12N2O
• Molecular Weight: 224.262
• Mol File: 69445-55-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1H-Benzimidazole, 6-methoxy-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole, 6-methoxy-1-phenyl-(69445-55-2)
• EPA Substance Registry System: 1H-Benzimidazole, 6-methoxy-1-phenyl-(69445-55-2)

Safety Data

• Hazardous Substances Data: 69445-55-2(Hazardous Substances Data)

Upstream product

• 64-18-6 formic acid 
• 82582-23-8 4-methoxy-N²-phenylbenzene-1,2-diamine 
• 36242-53-2 1-methoxy-3-phenylamino-4-nitrobenzene 
• 122-51-0 orthoformic acid triethyl ester 
• 108-86-1 bromobenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 4887-80-3 5-methoxy-1H-benzimidazole 
• 591-50-4 iodobenzene 
• 462-06-6 fluorobenzene 
• 27080-53-1 4-methoxy-1H-benzo[d]imidazole 
• 214279-40-0 3-iodo-4-nitroanisol 
• 103-70-8 Formanilid 

Relevant articles and documents

Ni-Catalyzed Dual C-H Annulation of Benzimidazoles with Alkynes for Synthesis of π-Extended Heteroarenes

Transition metal catalyzed dual C-H activation and annulation with alkynes was an attractive protocol to construct polycyclic π-extended structures. However, most of them were dominated by noble metal catalysts. Disclosed herein was the study of base-metal Ni-catalysis for dual C-H annulation of N-aromatic imidazole, which produced a range of desired polycyclic aza-quinolines in 48-95% yields. The use of bifunctional phosphine oxide ligand proved to be critical for success.

A versatile approach to ullmann C-N couplings at room temperature: New families of nucleophiles and electrophiles for photoinduced, copper-catalyzed processes

The use of light to facilitate copper-catalyzed cross-couplings of nitrogen nucleophiles can enable C-N bond formation to occur under unusually mild conditions. In this study, we substantially expand the scope of such processes, establishing that this approach is not limited to reactions of carbazoles with iodobenzene and alkyl halides. Specifically, we demonstrate for the first time that other nitrogen nucleophiles (e.g., common pharmacophores such as indoles, benzimidazoles, and imidazoles) as well as other electrophiles (e.g., hindered/deactivated/heterocyclic aryl iodides, an aryl bromide, an activated aryl chloride, alkenyl halides, and an alkynyl bromide) serve as suitable partners. Photoinduced C-N bond formation can be achieved at room temperature using a common procedure with an inexpensive catalyst (CuI) that does not require a ligand coadditive and is tolerant of moisture and a variety of functional groups.

A REGIOSELECTIVE COPPER CATALYZED SYNTHESIS OF BENZIMIDAZOLES AND AZABENZIMIDAZOLES

The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R0; R1; R2; R3; R4; R5; A1; A2; A3; A4; Q and J have the meanings indicated in the claims. The present invention provides a direct copper catalyzed regioselective process to a wide variety of unsymmetrical, multifunctional N/-substituted benzimidazoles or azabenzimidazoles of formula I starting from 2-halo-nitroarenes and N/-substituted amides. The process is useful for the production of pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.