2622-89-1

Usage

Uses

Used in Chemical Catalysts:
Diphenyl borinic acid is used as a catalyst in various organic transformations, facilitating reactions that would otherwise be difficult or inefficient. Its ability to act as a catalyst is crucial in the synthesis of complex organic molecules and pharmaceuticals.
Used in the Suzuki Coupling Reaction:
In the field of organic chemistry, diphenyl borinic acid is used as a catalyst for the Suzuki coupling reaction, a cross-coupling reaction between an organoboron compound and an organohalide to form carbon-carbon bonds. This reaction is widely used in the synthesis of biologically active compounds and materials.
Used in Hydroboration of Alkenes:
Diphenyl borinic acid also serves as a catalyst in the hydroboration of alkenes, a reaction that adds a hydroboron group to an alkene, leading to the formation of organoborane compounds. This reaction is essential in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Polymer Synthesis:
In the polymer industry, diphenyl borinic acid is used in the synthesis of block copolymers, which are polymers consisting of alternating or connected blocks of different polymer chains. These block copolymers exhibit unique properties, such as self-assembly and responsiveness to stimuli, making them suitable for applications in drug delivery, nanotechnology, and materials science.
Used as a Polymer Stabilizer:
Diphenyl borinic acid also functions as a stabilizer in polymers, enhancing their resistance to degradation, oxidation, and thermal stress. This stabilization is crucial for extending the lifetime and performance of polymer-based materials in various applications, including plastics, coatings, and adhesives.

InChI:InChI=1/C12H11BO/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14H

Upstream product

• 102-24-9 cyclotriboric acid trimethyl ester 
• 16500-38-2 tris(isobutyloxy) boroxine 
• 75-91-2 tert.-butylhydroperoxide 
• 960-71-4 triphenylborane 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 4426-21-5 oxybis(diphenylborane) 
• 20988-55-0 1-(pyridine-2-yl)ethanol 
• 6000-44-8 sodium glycinate 
• 13325-10-5 4-Aminobutanol 
• 4048-33-3 6-amino-1-hexanol 
• 4620-70-6 2-[(1,1-dimethylethyl)amino]-ethanol 
• 141-43-5 ethanolamine 
• 7568-93-6 2-Amino-1-phenylethanol 
• 629-05-0 n-octyne 

Downstream Products

• 98882-69-0 diphenyl-propoxy-borane 
• 99673-22-0 octyloxy-diphenyl-borane 
• 4426-21-5 oxybis(diphenylborane) 
• 3262-89-3 triphenylboroxine 
• 71-43-2 benzene 
• 98-80-6 phenylboronic acid 
• 524-95-8 2-Aminoethoxydiphenylborane 
• 109697-22-5 phenoxy-diphenyl-borane 
• 20692-68-6 [diethyl-bis-(2-hydroxy-ethyl)-ammoniumato^(1-)-O,O']-diphenyl-boron 
• 20692-59-5 5,5-trimethylene-2,2-diphenyl-1,3-dioxa-5-azonia-2-boratacyclohexane 
• 20692-60-8 8,8-diphenyl-7,9-dioxa-5-azonia-8-borata-spiro[4.5]decane 
• 20692-62-0 3,3-diphenyl-2,4,9-trioxa-6-azonia-3-borata-spiro[5.5]undecane 
• 3307-57-1 diphenylborinic acid morpholin-4-yloxymethyl ester 
• 3293-20-7 diphenylborinic acid 1-methyl-2-morpholin-4-yloxy-ethyl ester 

Relevant academic research and scientific papers

Synthesis and characterization of boron complexes of imidazo[1,5-a] pyridylalkyl alcohols

Imidazo[1,5-a]pyridin-1-ylalkyl alcohols were reacted with diphenylborinic acid to give boron complexes in which nitrogen and oxygen atoms were coordinated to a boron atom. The use of imidazo[1,5-a]pyridin-1-ylalkyl alcohol with two 2-pyridyl groups also

Boron Schiff bases derived from α-amino acids as nucleoli/cytoplasm cell-staining fluorescent probes: In vitro

The size, shape, and number of nucleoli in a cell's nucleus might help to distinguish a malignant from a benign tumor. Cellular biology and histopathology often require better visualization to understand nucleoli-related processes, thus organelle-specific fluorescent markers are needed. Here, we report the design, synthesis, and fully chemo-photophysical characterization of fluorescent boron Schiff bases (BOSCHIBAs), derived from α-amino acids (i.e., phenylalanine, tyrosine and tryptophan), with nucleoli- and cytoplasm-specific staining in cells. It is the first time that Boron Schiff bases derived from α-amino acids act as notorious dual (nucleoli and cytoplasm) cell-staining fluorescent probes. The boron derivatives not only showed good photostability and acceptable quantum yields (～5%) in solution, but also exhibited low cytotoxicity (>90% cell viability at 0.1 and 1 μg mL-1), which make them good candidates to be used in medical diagnosis. This journal is

(+)-(S)-trujillon, (+)-(S)-4-(2,2-diphenyl-1,3,2-oxazabolidin-5-oxo) propionic acid, a novel glutamatergic analog, modifies the activity of globus pallidus neurons by selective NMDA receptor activation

Decreased levels of glutamate and changes in several markers of glutamatergic function occur in movement disorders and chronic psychiatric illnesses. Ionotropic glutamate receptors have been implicated in neuronal cell death, and have, therefore, been related to the process of neurodegenerative diseases. Drugs that interact with the glutamatergic system are important tools for the development of better therapies. We examined the effect of a new glutamatergic analog, (+)-(S)-4-(2,2-diphenyl-1,3,2-oxazabolidin-5-oxo)propionic acid, (+)-(S)-Trujillon, on the spontaneous globus pallidus neuronal activity of the anesthetized rat. (+)-(S)-Trujillon excited most pallidal neurons in a dose-dependent manner. Furthermore, blockade of NMDA receptors (NMDARs) inhibited the (+)-(S)-Trujillon-induced excitation, whereas blockade of AMPA/kainate receptors did not. In addition, computational docking studies showed micromolar-range affinities of (+)-(S)-Trujillon for NR2A NMDARs. Our results indicate that (+)-(S)-Trujillon selectively activates NMDARs, an effect that could prove to be a useful tool in the analysis of motor, behavioral, and cognitive disorders, where NMDAR-mediated signaling is altered. Copyright

In situ measurements of tetraphenylboron degradation kinetics on clay mineral surfaces by IR

An attenuated total reflectance Fourier transform infrared (ATR-IR) spectroscopic method has been developed to quantitatively measure, in situ, the surface-facilitated degradation of tetraphenylboron (TPB) in fully aquated clay pastes. Two pathways for degradation of TPB could be studied both independently and simultaneously. Surface-facilitated oxidation of TPB to diphenylboric acid (DPBA) at Lewis acid sites on clay mineral surfaces was investigated on three members of the smectite family of clays. -from Authors

Bright and Stable NIR-II J-Aggregated AIE Dibodipy-Based Fluorescent Probe for Dynamic In Vivo Bioimaging

Organic dyes emitting in the second near-infrared (NIR-II, 900–1700 nm) window, with high molar extinction coefficients (MEC) and quantum yields (QY) in aqueous, are essential for in vivo bioimaging and biosensing. In this work, we developed a dibodipy-based aggregation-induced emission (AIE) fluorescent probe, THPP, to meet this aim. THPP exhibits a high MEC and has intensified absorption and emission in J-aggregated state, which significantly enhance the fluorescence intensity (≈55 folds) and extend the maximal absorption/emission wavelengths to 970/1010 nm in NIR-II region. Based on the bright THPP, imaging with a high frame rate (34 frames per second) at a deep “valid penetration depth” up to 6 mm can be achieved. This enabled simultaneous and dynamic imaging of vasculatures and deep tissues. Besides, we succeeded in monitoring the respiratory rate of acute-lung-injury mice and tracing the collateral circulation process with a high frame rate.

Structural requirements of 1-(2-pyridinyl)-5-pyrazolones for disproportionation of boronic acids

We observed an unusual formation of four-coordinate boron(III) complexes from the reaction of 1-(2-pyridinyl)-5-pyrazolone derivatives with arylboronic acids in the basic media. The exact mechanism is not clear; however, the use of unprotected boronic acid and the presence of a bidentate ligand appeared to be the key structural requirements for the transformation. The results suggest that base-promoted disproportionation of arylboronic acid with the assistance of the [N,O]-bidentate ligation of 1-(2-pyridinyl)-5-pyrazolone should take place and facilitate the formation of pyrazole di-arylborinate. Experiments to obtain a deeper understanding of its mechanism are currently underway.

COMPOUNDS AND METHODS FOR THE TREATMENT OF PATHOGENIC NEISSERIA

Tetracoordinate organoborate compounds, such as compounds harboring a tetraarylborate anion or a triarylalkylborate anion, are shown to exhibit a selective bacteriostatic and bactericidal effect against pathogenic Neisseria species such as N. meningitidis

A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C-H Alkylation of Alcohols

The development of catalyst-controlled, site-selective C(sp 3)-H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid-ethanolamine complex enhances the chemical yield of the α-C-H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched-peptides.

Palladium-catalyzed B-diarylation of diethylaminoborane for the synthesis of diarylborinic acids

The palladium-catalyzed synthesis of diarylborinic acid derivatives by intermolecular cross-coupling between aryl iodides and (amino)dihydrideborane is reported. The key to success of the reaction is the use of a less bulky diethylaminoborane reagent, which facilitates the second B-arylation.

Bis-aminocyclopropenylidene carbene borane catalyzed imine hydrogenation

Certain borenium cations supported by carbenes can function as hydrogenation catalysts for imines. While many carbenes have been explored, variation of the other groups on boron has been less common. We have investigated several carbene-borane adducts in an attempt to understand the ability of a bis-amino cyclopropenylidene (BAC) carbene dicyclohexylborane adduct to hydrogenate relatively sterically unhindered benzyl imines. As an additional variant, a BAC carbene adduct of diphenylborane was prepared. A convenient preparation of diphenylboron fluoride via a potassium fluoroborinate salt was employed in this chemistry. Reaction of diphenylboron fluoride with a BAC carbene afforded a modest yield of a carbene-fluoroborane adduct. Reaction between the fluoroborinate salt and a lithium tetrafluoroborate adduct of the carbene provided the adduct in much improved yield and cleanliness, and the product was structurally characterized. The fluoroborate could be converted to a boron hydride through fluoride-hydride exchange with dimethylchlorosilane. The boron hydride adduct was also structurally characterized. Unlike the BAC carbene dicyclohexylborane adduct, the BAC carbene diphenylborane adduct showed essentially no activity in hydrogenation of imines or enamines.