2033-30-9

Usage

Uses

Used in Pharmaceutical Industry:
5,6-DIMETHYL-2-BENZIMIDAZOLINONE is used as a key intermediate for the synthesis of pharmaceutically active compounds. Its incorporation into these compounds contributes to their overall efficacy and therapeutic potential.
Used in Biotechnology Industry:
5,6-DIMETHYL-2-BENZIMIDAZOLINONE is also used as a building block for the development of biologically active molecules, which can be applied in various biotechnological applications, such as the creation of novel bioactive agents for targeted drug delivery and the development of new therapies for various diseases.

InChI:InChI=1/C9H10N2O/c1-5-3-7-8(4-6(5)2)11-9(12)10-7/h3-4H,1-2H3,(H2,10,11,12)

Upstream product

• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 57-13-6 urea 
• 70254-61-4 4-hydroxy-6-methyl-2H-pyran-2-one 
• 71-36-3 butan-1-ol 
• 1711-61-1 5-(4-chlorophenyl)-3H-[1,3,4]oxadiazol-2-one 
• 103-71-9 phenyl isocyanate 
• 917-61-3 sodium isocyanate 
• 83-01-2 diphenylcarbamic chloride 
• 530-62-1 1,1'-carbonyldiimidazole 
• 124-38-9 carbon dioxide 
• 610-23-1 4,5-dimethyl-1,2-dinitrobenzene 
• 582-60-5 5,6-dimethyl-1H-benzo[d]imida-zole 

Downstream Products

• 184832-31-3 2-chloro-5,6-dimethyl-1-(phenylmethyl)-1H-benzimidazole 
• 39791-97-4 2-chloro-1,5,6-trimethyl-1H-benzo[d]imidazole 
• 39791-96-3 2-chloro-5,6-dimethyl-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

PrVO4/SnD NPs as a Nanocatalyst for Carbon Dioxide Fixation to Synthesis Benzimidazoles and 2-Oxazolidinones

Recently CO2 stabilization has received a great deal of attention because of its probable applications as a rich C1 resource and the synthesis of several fine chemicals can be accomplished through this stabilization. In this study, Sn(IV) doping dendritic fibrous nanosilica (SnD) supported PrVO4 nanoparticles as a catalyst (PrVO4/SnD) was synthesized by a in-situ procedure. The SnD with the ratios of Si/Sn in a variety of 6 to 40 were acquired through direct hydrothermal synthesis (DHS), and PrVO4 NPs on the surfaces of SnD were reduced in-situ. X-Ray diffraction (XRD), Scanning electron microscope (SEM), Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), and X-ray energy dispersive spectroscopy (EDS) were deployed for identifying the PrVO4/SnD. It is potentially a highly dynamic catalyst in the stabilization of CO2 for the production of 2-oxazolidinones and benzimidazoles. In addition, the catalyst is very easy to recycle and reuse without significant loss of active site Cu metal. Graphic Abstract: PrVO4/SnD NPs as a nanocatalyst for carbon dioxide fixation to synthesis benzimidazoles and 2-oxazolidinones. [Figure not available: see fulltext.]

CdSnO3/SnD NPs as a Nanocatalyst for Carbonylation of o-Phenylenediamine with CO2

In order to carbonize o-phenylenediamine with CO2, an effective approach was used with UV light irradiation by Sn(IV) doping DFNS (SnD) supported CdSnO3 as a catalyst (CdSnO3/SnD). In this catalyst, SnD with the ratios of Si/Sn in the range of 6 to 50 were obtained using the Direct Hydrothermal Synthesis (DHS), and the nanoparticles of CdSnO3 on the surfaces of SnD were reduced in situ. Scanning Electron Microscope (SEM), X-ray Diffraction (XRD), Fourier Transform Infrared Spectroscopy (FT-IR), X-ray Energy Dispersive Spectroscopy (EDS), and Transmission Electron Microscopy (TEM) were utilized for characterizing CdSnO3/SnD. It was found that CdSnO3/SnD nanostructures could be used for synthesizing o-phenylenediamines due to their effective and novel catalytic behavior through the reaction between o-phenylenediamines and CO2. Graphic Abstract: [Figure not available: see fulltext.]

Application of sea urchin-shaped cobalt-based photocatalyst in synthesis of benzoazacycle by converting CO2

The invention relates to the technical field of photocatalysis, in particular to application of a sea urchin-shaped cobalt-based photocatalyst to synthesis of benzoazacycle by converting CO2. A complex is of a sea urchin-shaped microsphere structure, which is composed of an organic ligand L and cobalt nitrate hexahydrate and is formed by arranging a plurality of nano needle-shaped complex crystals. The main body of the organic ligand L is p-aminobenzoic acid; the application comprises the following steps: introducing CO2 into a solution containing o-phenylenediamine compounds, carrying out carbonylation reaction and cyclization with o-phenylenediamine compounds under the action of the urchin-shaped cobalt-based catalyst to generate the benzoazacycle compounds. The sea urchin-shaped microsphere structure cobalt-based catalyst formed by the obtained nano needle-shaped complex crystal has a very large specific surface area and high photocatalytic efficiency; when the photocatalyst is adopted to catalyze and activate CO2, the reaction for synthesizing the benzoazacycle by converting CO2 can be carried out at room temperature, so that the energy consumption is greatly reduced, and the cost is reduced.

Synthesis of benzimidazolones by immobilized gold nanoparticles on chitosan extracted from shrimp shells supported on fibrous phosphosilicate

Here we demonstrate the synthesis of benzimidazolones from o-phenylenediamines and carbon dioxide in the presence of gold nanoparticles supported on a composite material based on microcrystalline chitosan from shrimp shells and fibrous phosphosilicate (CS-FPS/Au). The results showed that the gold nanoparticles were stable with the P, N and O atoms of CS-FPS. The morphology and structure of FPS leads to a higher catalytic activity. The CS-FPS/Au NPs were thoroughly characterized using TEM, FESEM, TGA, FTIR, and BET.

Discovery and Structure-Based Optimization of Benzimidazole-Derived Activators of SOS1-Mediated Nucleotide Exchange on RAS

Son of sevenless homologue 1 (SOS1) is a guanine nucleotide exchange factor that catalyzes the exchange of GDP for GTP on RAS. In its active form, GTP-bound RAS is responsible for numerous critical cellular processes. Aberrant RAS activity is involved in ～30% of all human cancers; hence, SOS1 is an attractive therapeutic target for its role in modulating RAS activation. Here, we describe a new series of benzimidazole-derived SOS1 agonists. Using structure-guided design, we discovered small molecules that increase nucleotide exchange on RAS in vitro at submicromolar concentrations, bind to SOS1 with low double-digit nanomolar affinity, rapidly enhance cellular RAS-GTP levels, and invoke biphasic signaling changes in phosphorylation of ERK 1/2. These compounds represent the most potent series of SOS1 agonists reported to date.

Azole-Anion-Based Aprotic Ionic Liquids: Functional Solvents for Atmospheric CO2 Transformation into Various Heterocyclic Compounds

The chemical transformation of atmospheric CO2 is of great significance yet still poses a great challenge. Herein, azole-anion-based aprotic ionic liquids (ILs) were synthesized by the deprotonation of weak proton donors (e.g., 2-methylimidazole, 4-methylimidazole, and 2,4-dimethylimidazole) with tetrabutylphosphonium hydroxide, [Bu4P][OH]. We found that these ILs, such as [Bu4P][2-MIm], could activate atmospheric CO2 through the formation of carbamates. The resultant carbamate intermediates could further react with various types of substrate, including propargylic alcohols, 2-aminobenzonitriles, ortho-phenylenediamines, and 2-aminothiophenol, thereby producing α-alkylidene cyclic carbonates, quinazoline-2,4(1 H,3 H)-diones, benzimidazolones, and benzothiazoline, respectively, in moderate-to-good yields. Thus, we have achieved the transformation of CO2 at atmospheric pressure, and we expect this method to open up new routes for the synthesis of various oxygen-containing heterocyclic compounds under metal-free conditions.

DBU-based ionic-liquid-catalyzed carbonylation of o-phenylenediamines with CO2 to 2-benzimidazolones under solvent-free conditions

Herein, a new route was presented to synthesize 2-benzimidazolones via the carbonylation of o-phenylenediamines with CO2 catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-based ionic liquids under solvent-free conditions. DBU acetate ([DBUH][OAc]) displayed high efficiency for catalyzing the reactions of CO2 with o-phenylenediamines, and a series of benzimidazolones were obtained in high yields. It was demonstrated that [DBUH][OAc] could serve as a bifunctional catalyst for these reactions with the cation activating CO2 and the anion activating o-phenylenediamines. This protocol provides an effective and environmentally friendly alternative route for production of benzimidazolones, and extends the chemical utilization of CO2 in organic synthesis as well.

4-(2-Pyridyl)piperazine-1-benzimidazoles as potent TRPV1 antagonists

A series of 4-(2-pyridyl)piperazine-1-benzimidazole analogues based on compound 1 was synthesized and evaluated for TRPV1 antagonist activity in capsaicin-induced (CAP) and pH 5.5-induced (pH) FLIPR assays in a human TRPV1-expressing HEK293 cell line. Potent TRPV1 antagonists were identified through SAR studies. From these studies, several antagonists were found, with IC50 values ranging from 32 nM to ～5000 nM. Among these, 11 [IC50 = 90 nM (CAP) and 104 nM (pH)] was further evaluated and found to be orally available in rats (F% = 19.7).

New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation

A series of 2-piperazinylbenzimidazole derivatives were prepared and evaluated as 5-HT3 receptor antagonists. Their 5-HT3 receptor affinities were evaluated by radioligand binding assays, and their abilities to inhibit the 5-HT-induced Bezold-Jarisch reflex in anesthetized rats were determined. Compound 7e (lerisetron, pK(i) = 9.2) exhibited higher affinity for the 5- HT3 receptor than did tropisetron and granisetron, while compound 7q (pK(i) = 7.5) had very low affinity for this receptor, showing that substitution on the N1 atom of the benzimidazole ring is essential for affinity and activity. The effect of substitution on the aromatic ring of benzimidazole by several substituents in different positions is also discussed. A strong correlation between the 5-HT3 antagonistic activity of the studied compounds and the position of substitution on the aromatic ring was established. Thus, while the 4-methoxy derivative 7m showed weak affinity for the 5-HT3 receptor (pK(i) = 6.7), the 7-methoxy derivative 7n exhibited the highest affinity (pK(i) = 9.4). Compounds 7e and 7n are now under further investigation as drugs for the treatment of nausea and emesis evoked by cancer chemotherapy and radiation.

Various Syntheses of Benzimidazolin-2-ones and Benzimidazoline-2-thiones under Microwave Irradiation

A variety of reagents (i-ix) which can be considered as carbonyl sources reacted with o-phenylenediamines to give high yields of benzimidazolin-2-ones and benzimidazoline-2-thiones on brief microwave irradiation.