710348-69-9

Basic information

• Product Name: 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester
• Synonyms: 2H-BenziMidazol-2-one, 1,3-dihydro-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benziMidazol-2-one;2-Oxo-2,3-dihydro-1H-benzoiMidazole-5-boronic acid;2,3-Dihydro-2-oxo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole, 1,3-Dihydro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzimidazol-2-one;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen (2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)boronate;5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydrobenzimidazol-2-one;2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester;5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3- dihydro-benzoimidazol-2-one
• CAS NO: 710348-69-9
• Molecular Formula: C₁₃H₁₇BN₂O₃
• Molecular Weight: 260.1
• Mol File: 710348-69-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 304.6°C at 760 mmHg
• Flash Point: 138°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 0.000867mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester(710348-69-9)
• EPA Substance Registry System: 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester(710348-69-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 710348-69-9(Hazardous Substances Data)

Usage

General Description

2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester is a chemical compound that belongs to the boronic acid pinacol ester family. It is a white crystalline powder with the molecular formula C14H18BNO3. 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester is often used in organic synthesis and medicinal chemistry as a building block for creating various compounds such as pharmaceuticals and agrochemicals. It has the potential to form boronate esters with diols, which can be utilized in cross-coupling reactions for the synthesis of complex organic molecules. Additionally, this chemical has shown promising antitumor and antiviral activities, making it an interesting target for further research and development.

InChI:InChI=1/C13H17BN2O3/c1-12(2)13(3,4)19-14(18-12)8-5-6-9-10(7-8)16-11(17)15-9/h5-7H,1-4H3,(H2,15,16,17)

Upstream product

• 39513-26-3 5-bromo-1,3-dihydro-benzoimidazol-2-one 
• 73183-34-3 bis(pinacol)diborane 
• 851883-08-4 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzene-1,2-diamine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 833486-94-5 4-amino-3-nitrophenylboronic acid pinacol ester 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 

Downstream Products

• 1062163-95-4 5-[1-(1-benzyl-piperidin-4-yl)-4-morpholin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-1,3-dihydro-benzoimidazol-2-one 
• 1059064-02-6 3-(2-bromobenzyl)-7-chloro-1-methyl-5-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one 
• 1463055-71-1 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole 
• 1257250-81-9 N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-amine 
• 1613638-64-4 5-[5-((R)-2-hydroxy-1-phenylethylamino)pyridin-3-yl]-1,3-dihydrobenzoimidazol-2-one 

Relevant articles and documents

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.

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.

IMIDAZOPYRAZINES AND PYRAZOLOPYRIMIDINES AND THEIR USE AS AMPA RECEPTOR MODULATORS

Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, [Formula should be inserted here] Also provided herein are pharmaceutical compositions, comprising compounds of Formula (I), and methods of