39513-26-3

Usage

Uses

Used in Pharmaceutical Preparation:
5-Bromo-1,3-dihydrobenzoimidazol-2-one is used as an intermediate in the synthesis of various pharmaceuticals for its ability to participate in multiple organic reactions, contributing to the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 5-Bromo-1,3-dihydrobenzoimidazol-2-one is utilized as a reagent, facilitating the creation of a variety of organic compounds through its reactive properties.
Used in Medicinal Chemistry and Drug Discovery:
5-Bromo-1,3-dihydrobenzoimidazol-2-one is employed as a building block in the production of complex organic molecules, particularly in medicinal chemistry, where its structural features and potential pharmacological properties are leveraged to discover and develop new therapeutic agents.
Used in Research and Development:
5-Bromo-1,3-dihydrobenzoimidazol-2-one is also used in research and development settings to explore its potential applications and to understand its reactivity and interactions with other molecules, which can lead to innovative approaches in drug design and synthesis.

InChI:InChI=1/C7H5BrN2O/c8-4-1-2-5-6(3-4)10-7(11)9-5/h1-3H,(H2,9,10,11)

Upstream product

• 75-44-5 phosgene 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 28230-35-5 5-Brom-anthranilsaeurehydroxamsaeure 
• 144167-55-5 5-bromo-1-(N-carbethoxyimidoyl)-2-benzimidazolone 
• 10468-46-9 N-(4-bromophenyl)hydroxylamine 
• 615-16-7 1H-benzimidazol-2-ol 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 875-51-4 4-Bromo-2-nitroaniline 
• 57-13-6 urea 
• 124-38-9 carbon dioxide 
• 1885-14-9 phenyl chloroformate 
• 144167-28-2 α-amino-α-carbethoxy-N-(4-bromophenyl)-nitrone 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 683240-76-8 6-bromo-2-chloro-1H-benzo[d]imidazole 
• 710348-69-9 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 100381-95-1 5-phenyl-1H-benzo[d]imidazol-2(3H)-one 
• 106429-59-8 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde 
• 33609-42-6 5-benzyl-1,3-dihydro-2H-benzimidazol-2-one 

Relevant academic research and scientific papers

ORGANIC COMPOUND, AND ORGANIC LIGHT EMITTING DIODE AND ORGANIC LIGHT EMITTING DISPLAY DEVICE INCLUDING THE SAME

The present disclosure provides an organic compound of the following formula and an organic light emitting diode and an OLED device including the same.

Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis

Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.

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.]

SBA-15 Supported Dendritic ILs as a Green Catalysts for Synthesis of 2-Imidazolidinone from Ethylenediamine and Carbon Dioxide

In this work, a simple and facile approach is conducted for preparing many new SBA-15 supported dendritic imidazolium ILs heterogeneous catalysts SBA-15/IL(1–3) having high ionic density from SBA-15. SBA-15/IL(3) as a green heterogeneous catalyst can be used for synthesis of 2-imidazolidinone from ethylenediamine and carbon dioxide and considering solvent-free condition. SBA-15/IL(3) showed to have the highest catalytic activity besides a positive dendritic influence on the yields of the synthesis of 2-imidazolidinone in the presence of CO2 is seen because of existing the high-density peripheral zwitterionic ionic liquid functional groups on the biobased SBA-15/IL(3) catalyst surfaces. Graphical Abstract: [Figure not available: see fulltext.]

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.]

Micromolecular reversible BTK inhibitor for treating rheumatoid arthritis

The invention relates to a micromolecular reversible BTK inhibitor for treating rheumatoid arthritis, and specifically provides a compound. The compound is the compound as shown in a formula I, or a stereisomer, a geometrical isomer and a tautomer thereof, nitric oxide, aquo-complex, a solvate, a metabolite and pharmaceutically acceptable salts and prodrugs. The inventor finds that polysubstitutedquinolone compound or derivate thereof as shown in formula I can be used as the BTK inhibitor and is high in activity during treating rheumatoid arthritis.

Discovery of 4-Aminoquinoline-3-carboxamide derivatives as potent reversible Bruton's tyrosine kinase inhibitors for the treatment of rheumatoid arthritis

A structure-hopping strategy was applied to discover a series of novel 4-aminoquinoline-3-carboxamide derivatives as potent, reversible BTK inhibitors. Compared to the previously described cinnoline scaffold compounds, the 4-aminoquinoline analogues showed significantly improved drug-like properties, especially in their aqueous solubility. The most potent compound, 25, displayed a stronger inhibitory effect on both BTKWT (IC50 = 5.3 nM) and BTKC481S (IC50 = 39 nM). In a rodent collagen-induced arthritis model, compound 25 efficiently reduced paw swelling without a loss in body weight. On the basis of potency, drug-like properties, stability, and noncovalent mode of inhibition, our representative inhibitors could have a promising profile to be treatments for a wide range of autoimmune diseases.

Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3

Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.

Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source

A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.

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.