3652-96-8

Basic information

• Product Name: 2-(4-chloro-phenyl)-1,3-dimethyl-2,3-dihydro-1H-benzoimidazole
• Synonyms: 2-(4-chloro-phenyl)-1,3-dimethyl-2,3-dihydro-1H-benzoimidazole
• CAS NO: 3652-96-8
• Molecular Weight: 258.75
• Mol File: 3652-96-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(4-chloro-phenyl)-1,3-dimethyl-2,3-dihydro-1H-benzoimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chloro-phenyl)-1,3-dimethyl-2,3-dihydro-1H-benzoimidazole(3652-96-8)
• EPA Substance Registry System: 2-(4-chloro-phenyl)-1,3-dimethyl-2,3-dihydro-1H-benzoimidazole(3652-96-8)

Safety Data

• Hazardous Substances Data: 3652-96-8(Hazardous Substances Data)

Upstream product

• 29627-62-1 N,N’-dimethyl-N,N’-di(p-toluenesulfonyl)-o-phenylenediamine 
• 49633-28-5 1,2-bis-(p-methylphenylsulfonamido)-benzene 
• 74-88-4 methyl iodide 
• 7181-87-5 1,3-dimethylbenzimidazolium Iodide 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 3213-79-4 N,N'-dimethyl-1,2-phenylenediamine 

Downstream Products

• 100672-48-8 4-Chloro-N-methyl-N-(2-methylamino-phenyl)-benzamide 
• 4217-54-3 9,10-dihydro-10-methylacridine 
• 46865-17-2 2-(4-chloro-phenyl)-1,3-dimethyl-benzoimidazolium 
• 104-88-1 4-chlorobenzaldehyde 

Relevant articles and documents

Mechanistic study on the solution-phase n-doping of 1,3-dimethyl-2-aryl-2, 3-dihydro-1H-benzoimidazole derivatives

The discovery of air-stable n-dopants for organic semiconductor materials has been hindered by the necessity of high-energy HOMOs and the air sensitivity of compounds that satisfy this requirement. One strategy for circumventing this problem is to utilize stable precursor molecules that form the active doping complex in situ during the doping process or in a postdeposition thermal- or photo-activation step. Some of us have reported on the use of 1H-benzimidazole (DMBI) and benzimidazolium (DMBI-I) salts as solution- and vacuum-processable n-type dopant precursors, respectively. It was initially suggested that DMBI dopants function as single-electron radical donors wherein the active doping species, the imidazoline radical, is generated in a postdeposition thermal annealing step. Herein we report the results of extensive mechanistic studies on DMBI-doped fullerenes, the results of which suggest a more complicated doping mechanism is operative. Specifically, a reaction between the dopant and host that begins with either hydride or hydrogen atom transfer and which ultimately leads to the formation of host radical anions is responsible for the doping effect. The results of this research will be useful for identifying applications of current organic n-doping technology and will drive the design of next-generation n-type dopants that are air stable and capable of doping low-electron-affinity host materials in organic devices.

Marcus theory of a parallel effect on α for hydride transfer reaction between NAD+ analogues

Rate and equilibrium constants for hydride transfer from a series of 1,3-dimethyl-2-substituted phenylbenzimidazolines to a pyridinium ion, a quinolinium ion, and a phenanthridinium ion have been evaluated. Each oxidizing agent gives a linear Bronsted plot with slope, α. The α values vary systematically with the spontaniety of the reactions. They are in reasonable agreement with the predictions of modified Marcus theory. Their trend is very accurately predicted, showing a parallel (Leffler-Hammond) effect. These results make a multistep mechanism, involving high energy intermediates, very unlikely.

Synthesis and Autoxidation of 1,3-Dialkyl-2-arylbenzimidazolines

During the attempted studies of the elimination reactions of 1,3-dimethyl-(I, R = CH3)- and 1,3-diethyl-(I, R = C2H5)-2-arylbenzimidazolines, a novel rearrangement has been observed to take place resulting in substituted amides by autoxidative ring-opening.