717-57-7

Basic information

• Product Name: 1,2-Benzenediamine, N-(phenylmethylene)-
• CAS NO: 717-57-7
• Molecular Formula: C13H12N2
• Molecular Weight: 196.252
• Mol File: 717-57-7.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 1,2-Benzenediamine, N-(phenylmethylene)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Benzenediamine, N-(phenylmethylene)-(717-57-7)
• EPA Substance Registry System: 1,2-Benzenediamine, N-(phenylmethylene)-(717-57-7)

Safety Data

• Hazardous Substances Data: 717-57-7(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 100-52-7 benzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 41013-30-3 2,2'-[(1S,2S)-1,2-diphenyl-1,2-ethanediylbis(nitrilomethylidyne)]diphenol 
• 100-51-6 benzyl alcohol 
• 5822-13-9 N-benzyl-1,2-phenylenediamine 
• 127896-76-8 N-(1-chlorobenzyl)pyridinium chloride 

Downstream Products

• 716-79-0 2-phenyl-1H-benzoimidazole 
• 53088-00-9 2-phenyl-2,3-dihydro-1H-benzoimidazole 
• 80785-71-3 2,2'-diphenyl-1,1'-bibenzimidazole 
• 5822-13-9 N-benzyl-1,2-phenylenediamine 
• 15223-25-3 N,N-dibenzylidenebenzene-1,2-diamine 
• 95-54-5 1,2-diamino-benzene 
• 739-88-8 1-benzyl-2-phenyl-1H-1,3-benzimidazole 

Relevant articles and documents

Metal-free oxidative synthesis of benzimidazole compounds by dehydrogenative coupling of diamines and alcohols

We report a novel metal-free synthesis of benzimidazole compounds by dehydrogenative coupling of diamines and alcohols. Using NHPI as a nonmetallic catalyst combined with molecular oxygen or air as the oxidant, this transformation represents a widely applicable protocol to N-heterocycles, such as benzimidazoles, benzothiophenes, benzooxazoles and quinazolines. Flow microreactors operating under optimized conditions enabled this reaction with higher efficiency, and the total residence time was 30 min compared with the batch bubbling reactor (10 h). Moreover, a possible reaction mechanism is proposed according to the control experiments.

Direct synthesis of 2-substituted benzimidazoles: Via dehydrogenative coupling of aromatic-diamine and primary alcohol catalyzed by a Co complex

A Co(ii) complex with a stable structure was designed and synthesized with quinalic acid and Co (OAc)2·4H2O. The single crystal structure of the complex was characterized by X-ray diffraction. A dehydrogenative coupling of aromatic diamines and primary alcohols was developed by using the Co(ii) complex as the catalyst to synthesize 2-substituted benzimidazole. A series of 2-substituted benzimidazoles were obtained with good to excellent yields under mild reaction conditions. In addition, a compound with inhibitory Parkinson's activity was synthesized on a gram-scale by using this method. Finally, the reaction mechanism was proposed and the energy changes in the reaction process were simulated by density functional theory (DFT).

Visible-light-induced condensation cyclization to synthesize benzimidazoles using fluorescein as a photocatalyst

A mild strategy for visible-light-induced synthesis of benzimidazoles was developed using aromatic aldehydes and o-phenylenediamines as substrates. The use of an organic dye, fluorescein, as an innoxious photocatalyst provided a mild and inexpensive catalytic system to synthesize a series of benzimidazoles in moderate to excellent yields. It was originally applied to this system to obtain benzimidazoles. Besides, the catalytic system does not require an additional oxidant or metal which was good for the environment.