85573-17-7

Usage

InChI:InChI=1/C20H16N2O2/c23-16-9-5-14(6-10-16)13-22-19-4-2-1-3-18(19)21-20(22)15-7-11-17(24)12-8-15/h1-12,21,23H,13H2

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 74661-50-0 4,4′-[1,2-phenylenebis(nitrilomethylidene)]bisphenol 

Downstream Products

• 1313762-55-8 [RuCl₃(1-p-hydroxybenzyl-2-p-hydroxyphenylbenzimidazole)2(H₂O)2] 

Relevant academic research and scientific papers

Water extract of onion catalyst: An economical green route for the synthesis of 2-substituted and 1,2-disubstituted benzimidazole derivatives with high selectivity

An efficient, environmental friendly and substrate controlled method of synthesis of 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 with high selectivity has been achieved from the reaction of o-phenylenediamine 1 and aldehydes 2 in the presence of water extract of onion and selecting suitable reaction medium. This method is widely applicable for variety of aldehydes such as aromatic/aliphatic/heterocyclic aldehydes and 1,2-diamines to afford 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 in good to excellent yields (up to 96%). The developed method of water extract of onion catalysis produced 2-substituted benzimidazoles 3 from aromatic aldehydes having electron-withdrawing groups, whereas aromatic aldehydes bearing electron donating groups selectively furnished 1,2-disubstituted benzimidazole 4 derivatives. The process described here has several advantages of cheap, low energy consumption, commercially available starting materials, operational simplicity and nontoxic catalyst. The use of water extract of onion makes this present methodology green and giving a useful contribution to the existing methods available for the preparation of benzimidazole derivatives. In addition, Hammett correlation of substituent constant (σ) vs percentage (%) yield has been established.

MWCNTs-ZrO2 as a reusable heterogeneous catalyst for the synthesis of N-heterocyclic scaffolds under green reaction medium

A simple, efficient, and facile heterogeneous multi-walled carbon nanotubes-zirconia nanocomposite (MWCNTs-ZrO2) has been synthesized using natural feedstock coconut juice (água-de-coco do Ceará). The synthesized catalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, and X-ray photoelectron spectroscopy analysis. The heterogeneous nanocomposite has been used for one-pot synthesis of various N-heterocyclic compounds like pyrazoles, 1,2-disubstituted benzimidazoles, 2-arylbenzazoles, and 2,3-dihydroquinazolin-4(1H)-ones under green reaction medium at room temperature. This novel method has several advantages, such as short reaction time, simple work-up, excellent yield, and green reaction conditions. The catalyst was recycled up to four times without significant loss in catalytic activity.

Highly efficient chemoselective synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles by using TiCp2Cl2 catalyst

One pot highly efficient chemoselective N-arylmethyl benzimidazole has been prepared by using catalyst TiCp2Cl2 in tetrahydrofuran solvent smoothly. This method is very much effective for the condensation between different aldehydes

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

Synthesis and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of 2,4,5–trisubstituted imidazoles, benzo[d]imidazoles, benzo[d] oxazoles and azo-linked benzo[d]oxazoles

Amino glucose-functionalized silica-coated NiFe2O4 nanoparticles (NiFe2O4@SiO2@amino glucose) were chemically synthesized and characterized by transmission electron microscope (TEM), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), energy dispersive X-ray analysis (EDX), vibrating sample magnetometer (VSM), Zetasizer and Fourier transform infrared spectroscopy (FT-IR) instruments. NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of 2,4,5-trisubstituted imidazoles through one-pot multicomponent condensation of benzil or benzoin, ammonium acetate with aryl aldehydes and for the synthesis of benzoxazoles using condensation reaction of 2-aminophenol with aryl aldehydes under solvent free condition. In the other study, this synthesized magnetically reusable catalyst was introduced as a new avenue for the synthesis of benzo[d]imidazoles using the reaction between aryl aldehydes and 1,2-diaminobenzene. These compounds were obtained in high yields and short reaction times. The catalyst could be easily recovered and reused for five cycles with almost consistent activity. Synthesized compounds were characterized by their physical constant, comparison with authentic samples, FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.

Natural bio-surfactant for pseudomulticomponent synthesis of 2-aryl-1-aryl methyl-1H-benzimidazoles

Green chemistry emphasizes the development of environmentally benign chemical processes and technologies. Pseudo-multicomponent synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using o-phenylenediamine and aromatic aldehydes is carried out by Br?nsted acid type bio-surfactant as a catalyst. The green features of this method include the use of biodegradable catalyst obtained from renewable resource i.e. Citrus Limonium extract as bio-surfactant type Br?nsted acid, which provides a micellar media for effective cyclocondensation. The critical micellar concentration (cmc) of biosurfactant was determined by conductivity method and visualized by light microscopy measurement. Identity of all pure compounds was ascertained on the basis of FT-IR, 1H NMR and 13C NMR spectroscopic techniques.

Mesoporous silica supported ytterbium as catalyst for synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzimidazoles

The benzimidazole ring is an important pharmacophore in contemporary drug discovery. Thus, effort to identifying new compounds containing benzimidazole scaffolds have gained much attention in recent years. In the present study, MCM-41 type mesoporous silica with large pore (l-MSN) supported ytterbium was successfully prepared by wet impregnation method. Among rare earth metal salts, ytterbium triflate has already been widely investigated as a catalyst in organic synthesis but less toxic ytterbium oxide has yet to be explored. Relatively high abundance and low cost of ytterbium with respect to many catalytically active metals (e.g. Pd, Au, Ru, Ir, Pt) offer an opportunity to develop sustainable catalysts for organic conversions. The catalyst has been characterized by various techniques including nitrogen adsorption, FT-IR, TEM, SEM, EDX technique and elemental mapping. The obtained materials exhibit high surface area and a narrow distribution of mesoporosity. The catalytic performance of the Yb@l–MSNs was tested by synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzimidazoles through the coupling of aldehydes with o-phenylenediamine. The catalyst resulted in excellent yields in short reaction times and the reaction showed tolerance toward both electron-donating and electron-withdrawing functional groups at room temperature. A particularly interesting finding was the solvent selectivity of this reaction; namely, 1,2-disubstituted benzimidazoles generated as major product in water-ethanol, while the 2-substituted benzimidazoles was generated exclusively in non-polar solvents like toluene.

KIT-6 Mesoporous Silica-coated Magnetite Nanoparticles: A Highly Efficient and Easily Reusable Catalyst for the Synthesis of Benzo[d]imidazole Derivatives

KIT-6 mesoporous silica-coated magnetite nanoparticles as highly ordered large-pore nanoparticles supply an environmentally friendly procedure for the synthesis of benzo[d]imidazoles through condensation of 1,2-diaminobenzene with aryl aldehydes. These co

1,4-Diazabicyclo [2.2.2] octanium diacetate: As an effective, new and reusable catalyst for the synthesis of benzo[d]imidazole

A general synthetic route to benzo[d]imidazoles has been developed using 1,4-diazabicyclo [2.2.2] octanium diacetate as a new bis ionic liquid under thermal and solvent free condition. The union of two fragments including one equivalent of various aldehydes and one equivalent of 1,2-phenylenediamine was accomplished by an efficient and convenient protocol enabling the synthesis of benzo[d]imidazoles in excellent yields. The major advantages of the present method are: less reaction times, high yields, and easy purification of the products, solvent-free conditions, environmental friendliness, and convenient operation.

Chemoselective synthesis of 1,2-disubstituted benzimidazoles in lactic acid without additive

Lactic acid is recognised as a biocompatible medium for the chemoselective synthesis of the 1,2-disubstituted benzimidazole scaffold via a direct one-pot cyclocondensation of o-phenylenediamine with aldehydes. Various 1,2-disubstituted benzimidazole deriv