3659-77-6

Basic information

• Product Name: 4-METHYL-2-PHENYLBENZIMIDAZOLE
• Synonyms: 4-METHYL-2-PHENYLBENZIMIDAZOLE
• CAS NO: 3659-77-6
• Molecular Formula: C₁₄H₁₂N₂
• Molecular Weight: 208.263
• Mol File: 3659-77-6.mol
• Article Data: 37

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-METHYL-2-PHENYLBENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-2-PHENYLBENZIMIDAZOLE(3659-77-6)
• EPA Substance Registry System: 4-METHYL-2-PHENYLBENZIMIDAZOLE(3659-77-6)

Safety Data

• Hazardous Substances Data: 3659-77-6(Hazardous Substances Data)

Upstream product

• 73902-63-3 N-(2-methyl-6-nitrophenyl)benzamide 
• 36954-10-6 N-o-tolyl-benzamide oxime 
• 98-09-9 benzenesulfonyl chloride 
• 57327-73-8 N-(o-tolyl)benzimidamide 
• 107411-08-5 1-(o-tolyl)-5-phenyltetrazole 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 2687-25-4 3-methyl-1,2-benzenediamine 
• 52379-50-7 N-(3-methylphenyl)-benzamidine 
• 100-47-0 benzonitrile 
• 108-44-1 1-amino-3-methylbenzene 
• 100-51-6 benzyl alcohol 
• 570-24-1 2-Methyl-6-nitroaniline 
• 100-46-9 benzylamine 

Downstream Products

• 1417819-40-9 11-methyl-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline 
• 1370000-27-3 C₁₄H₁₀N₂O 
• 1370000-19-3 C₁₉H₂₁N₃ 

Relevant articles and documents

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Preparation method of 2-substituted benzimidazole compound

The invention discloses a preparation method of a 2-substituted benzimidazole compound, and belongs to the field of synthesis of benzimidazole compounds. The 2-substituted benzimidazole compound is synthesized in an organic solvent by taking an o-nitroaniline compound, aromatic aldehyde, o-dinitrobenzene and aromatic aldehyde as raw materials and taking Co particles wrapped by a nitrogen-doped carbon material as a catalyst. According to the method, the 2-substituted benzimidazole compound can be prepared at room temperature, the reaction conditions are mild, the yield is as high as 95%, the selectivity is as high as 99%, and the method is economical, environmentally friendly and wide in substrate applicability. The used catalyst is easy to prepare, low in cost and good in reusability, canbe separated by utilizing magnetism, and is convenient to recover, so that the method has a relatively strong industrial application prospect.

Solvent-Free N-Alkylation and Dehydrogenative Coupling Catalyzed by a Highly Active Pincer-Nickel Complex

The synthesis and characterization of a pincer-nickel complex of the type (iPr2NNN)NiCl2(CH3CN) is reported here. We have demonstrated the utility of this pincer-nickel complex (0.02 and 0.002 mol %) for the catalytic N-alkylation of amines using various alcohols. Under solvent-free conditions, while the highest yield (ca. 90%) was obtained for the alkylation of 2-aminopyridine with naphthyl-1-methanol, excellent turnovers (34000 TONs) were observed for the alkylation of 2-aminopyridine with 4-methoxybenzyl alcohol. To demonstrate the synthetic utility of these systems, high-yield reactions (up to 98%) have been probed for representative substrates with a higher loading of the pincer-nickel catalyst (4 mol %). DFT studies indicate that while β-hydride elimination is the RDS for alcohol dehydrogenation, the N-alkylated product can be formed either via hydrogenation with a rate-determining σ-bond metathesis or by alcoholysis that has imine insertion as the RDS. All of the corresponding resting states have been observed by HRMS (ESI) analysis. The labeling experiments are also complementary to DFT studies and show evidence for the involvement of the benzylic C-H bond in the RDS with a kCHH/kCHD value of about 2.5. This method has been applied to accomplish efficient (2000 TONs) dehydrogenative coupling leading to various benzimidazoles.