15223-25-3

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 100-51-6 benzyl alcohol 
• 615-28-1 o-phenylenediamine dihydrochloride 
• 100-52-7 benzaldehyde 
• 64-17-5 ethanol 
• 717-57-7 N-benzylidene-o-phenylenediamine 

Downstream Products

• 739-88-8 1-benzyl-2-phenyl-1H-1,3-benzimidazole 
• 51592-02-0 o-amino-N-n-butylaminobenzene 
• 129674-89-1 HgI₂(bisbenzaldehyde-o-phenylenediamine) 
• 1432037-79-0 C₂₀H₁₆Cl₂N₂Pd 
• 21443-66-3 N¹,N²-dibenzylbenzene-1,2-diamine 
• 1292773-19-3 [{(3-diethoxyphosphoryl)(phenylmethyl)-2-oxo-2-phenyl-2,3-dihydro-2λ(5)-benzo[1,3,2]diazaphosphol-1-yl}(phenyl)methyl]phosphonic acid dimethyl ester 
• 1292773-07-9 [{(3-dimethoxyphosphoryl)(phenylmethyl)-2-oxo-2-phenyl-2,3-dihydro-2λ(5)-benzo[1,3,2]diazaphosphol-1-yl}(phenyl)methyl]phosphonic acid dimethyl ester 
• 129700-05-6 HgCl₂(bisbenzaldehyde-o-phenylenediamine) 
• 131300-13-5 HgBr₂(bisbenzaldehyde-o-phenylenediamine) 
• 129690-66-0 Hg(SCN)2(bisbenzaldehyde-o-phenylenediamine) 
• 129699-96-3 Hg(NO₃)2(bisbenzaldehyde-o-phenylenediamine) 
• 573979-51-8 N,N'-dipropyl-1,2-phenylenediamine 
• 55899-42-8 N-propylbenzene-1,2-diamine 

Relevant academic research and scientific papers

Mesoporous imine-based organic polymer: catalyst-free synthesis in water and application in CO2 conversion

A mesoporous imine-functionalized organic polymer (Imine-POP) was prepared based on the reaction of an aryl ammonium salt with an aromatic aldehyde in water without any catalyst and template. The Pd coordinated Imine-POP exhibited high catalytic activity for the N-formylation of amines with CO2/H2 at 100 °C, affording a series of formamides in high yields.

Facile Synthesis of 1,2-Disubstituted Benzimidazoles Usingp-Toluenesulfonic Acid through Grinding Method

Abstract: An efficient synthetic method for the highly selective synthesis ofpharmacologically active 1,2-disubstituted benzimidazole derivatives fromo-phenylenediamine and various aromaticaldehydes catalyzed by p-toluenesulfonic acidthrough grinding unde

A Zirconium Indazole Carboxylate Coordination Polymer as an Efficient Catalyst for Dehydrogenation-Cyclization and Oxidative Coupling Reactions

Rational ligand design is crucial for achieving widespread applications of coordination polymers. The preparation, structural characterisation, and catalytic applications of zirconium (IV) coordination polymer (Zr-IDA), which was derived from 1-(carboxymethyl)-1H-indazole-5-carboxylic acid are reported. The Zr-IDA catalyst contains porous and highly crystalline particles with a quasi-spherical morphology around 100 nm in size, and Zr was coordinated with both O and N as shown by FT-IR and XPS measurements. Importantly, the Zr-IDA catalyst shows great activity, selectivity and stability in the oxidative coupling of benzyl cyanides with tert-butyl hydroperoxide to afford tert-butyl peresters, and the dehydrogenation cyclization of o-phenylenediamines with aromatic alcohols to afford 1,2-disubstituted benzimidazole derivatives. Mechanistic investigations were carried out to study these reactions and the developed catalytic system in more detail.

Preparations of Saturated N-P-N Type Secondary Phosphine Oxides and their Applications in Cross-Coupling Reactions

A series of cyclohexane-1,2-diamine (3a-3d) and benzene-1,2-diamine derivatives (3e-3h) were pre- pared. Followed by hydrolysis, the reaction of 3a-3c with PCl3 successfully led to the formation of cor- responding metastable saturated heteroato

Visible-light-promoted synthesis of benzimidazoles

A simple and environmentally-friendly synthetic method for benzimidazoles, which are important structural motifs in many applications owing to their various biological functions, has been developed. The reaction of o-phenylenediamine and a variety of aliphatic/aromatic aldehydes in methanol proceeds at room temperature with only natural sources, molecular oxygen and visible light. A simple and eco-friendly synthetic method for benzimidazoles, which are important structural motifs in many applications owing to their various biological functions, has been developed. The reaction of o-phenylenediamine and a variety of aliphatic/aromatic aldehydes in methanol proceeds at room temperature with only natural sources, molecular oxygen and visible light. Copyright

Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity

Selectivity control during the formation of 1,2-disubstituted benzimidazoles has been achieved for the reaction of o-phenylenediamine with aldehydes in the presence of solid supported protic acids as catalysts and choosing an appropriate reaction medium. Perchloric acid adsorbed on silica-gel (HClO4-SiO2) was found to be the most effective catalyst system for the synthesis of 1,2-disubstituted benzimidazoles in EtOH at rt. Apart from the catalyst and solvent, the electronic and steric factors of the aldehyde and the electronic factor of the o-phenylenediamine are also significant contributory factors in dictating the selectivity. An understanding of the mechanistic course of the formation of the 1,2-disubstituted benzimidazoles has been outlined that would rationalise the origin of selectivity control under the set experimental parameters. The Royal Society of Chemistry.

γ-Maghemite-silica nanocomposite: A green catalyst for diverse aromatic N-heterocycles

γ-Maghemite-silica nanocomposite has been applied as a green catalyst to synthesize variety of aromatic N-heterocycles under solvent free conditions. Characterization was done by modern analytical tools (UV, IR, AAS, DSC, EDXRF, powdered XRD, EPR, Mo?ssbauer and TEM). Mild reaction conditions and recyclability have made the present protocol both environmentally and economically viable.

Hydrogen-bond-driven electrophilic activation for selectivity control: Scope and limitations of fluorous alcohol-promoted selective formation of 1,2-disubstituted benzimidazoles and mechanistic insight for rationale of selectivity

Hydrogen-bond-driven electrophilic activation for selectivity control during competitive formation of 1,2-disubstituted and 2-substituted benzimidazoles from o-phenylenediamine and aldehydes is reported. The fluorous alcohols trifluoroethanol and hexafluoro-2-propanol efficiently promote the cyclocondensation of o-phenylenediamine with aldehydes to afford selectively the 1,2-disubstituted benzimidazoles at rt in short times. A mechanistic insight is invoked by NMR, mass spectrometry, and chemical studies to rationalize the selectivity. The ability of the fluorous alcohols in promoting the reaction and controlling the selectivity can be envisaged from their better hydrogen bond donor (HBD) abilities compared to that of the other organic solvents as well as of water. Due to the better HBD values, the fluorous alcohols efficiently promote the initial bisimine formation by electrophilic activation of the aldehyde carbonyl. Subsequently the hydrogen-bond-mediated activation of the in situ-formed bisimine triggers the rearrangement via 1,3-hydride shift to form the 1,2-disubstituted benzimidazoles.

"All-water" chemistry of tandem N-alkylation-reduction- condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles

A water-assisted tandem N-alkylation-reduction-condensation process has been devised as a new synthetic route for the one-pot synthesis of N-arylmethyl-2-substituted benzimidazoles. Water plays the crucial and indispensable role through hydrogen bond mediated 'electrophile-nucleophile dual activation' in promoting selective N-monobenzylation of o-nitroanilines as an alternative to the transition metal-based chemistry for C-N bond formation (amination) and forms the basis of disposing the substituents on the benzimidazole moiety in regiodefined manner. Water also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C-N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation-reduction-condensation process exemplifies an 'all-water' chemistry for the synthesis of N-arylmethyl-2- substituted benzimidazoles.

Synthesis of functionalized benzimidazoles and quinoxalines catalyzed by sodium hexafluorophosphate bound Amberlite resin in aqueous medium

A very simple, eco-friendly, and versatile method for the selective synthesis of 1,2-disubstituted benzimidazoles and quinoxalines in water-methanol (1:1) mixture with the aid of resin bound hexafluorophosphate ion as catalyst is reported. The method is also effective for the incorporation of quinoxaline nucleus at the A ring of pentacyclic triterpenoid, friedelin. A plausible mechanism for the formation of disubstituted benzimidazole has also been suggested.