Category: 25240-59-9

de Gracia Lux, Caroline published the artcileBiocompatible Polymeric Nanoparticles Degrade and Release Cargo in Response to Biologically Relevant Levels of Hydrogen Peroxide, SDS of cas: 25240-59-9, the publication is Journal of the American Chemical Society (2012), 134(38), 15758-15764, database is CAplus and MEDLINE.

Oxidative stress is caused predominantly by accumulation of hydrogen peroxide and distinguishes inflamed tissue from healthy tissue. Hydrogen peroxide could potentially be useful as a stimulus for targeted drug delivery to diseased tissue. However, current polymeric systems are not sensitive to biol. relevant concentrations of H₂O₂ (50-100 μM). Here we report a new biocompatible polymeric capsule capable of undergoing backbone degradation and thus release upon exposure to such concentrations of hydrogen peroxide. Two polymeric structures were developed differing with respect to the linkage between the boronic ester group and the polymeric backbone: either direct (1) or via an ether linkage (2). Both polymers are stable in aqueous solution at normal pH, and exposure to peroxide induces the removal of the boronic ester protecting groups at physiol. pH and temperature, revealing phenols along the backbone, which undergo quinone methide rearrangement to lead to polymer degradation Considerably faster backbone degradation was observed for polymer 2 over polymer 1 by NMR and GPC. Nanoparticles were formulated from these novel materials to analyze their oxidation triggered release properties. While nanoparticles formulated from polymer 1 only released 50% of the reporter dye after exposure to 1 mM H₂O₂ for 26 h, nanoparticles formulated from polymer 2 did so within 10 h and were able to release their cargo selectively in biol. relevant concentrations of H₂O₂. Nanoparticles formulated from polymer 2 showed a 2-fold enhancement of release upon incubation with activated neutrophils, while controls showed a nonspecific response to ROS producing cells. These polymers represent a novel, biol. relevant, and biocompatible approach to biodegradable H₂O₂-triggered release systems that can degrade into small mols., release their cargo, and should be easily cleared by the body.

Journal of the American Chemical Society published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, SDS of cas: 25240-59-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ito, Masaki published the artcileSelective Boryl Silyl Ether Formation in the Photoreaction of Bisboryloxide/Boroxine with Hydrosilane Catalyzed by a Transition-Metal Carbonyl Complex, Safety of 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, the publication is Journal of the American Chemical Society (2014), 136(17), 6183-6186, database is CAplus and MEDLINE.

Selective B-O-Si bond formation was achieved in the reaction of bisboryloxide O(Bpin)₂ (pin = (OCMe₂)₂)/boroxine (MeBO)₃ system with tertiary silane R₃SiH in the presence of stoichiometric water and a catalytic amount of [M](CO)₅ ([M] = Mo(CO), W(CO), Fe) to give boryl silyl ethers. Moreover, this reaction can be applied to various hydrosilanes (disilyl compounds and secondary silanes) and hydrogermane. Some of the boryl silyl ethers thus formed were confirmed by X-ray anal.

Journal of the American Chemical Society published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Safety of 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ojha, Devi Prasan published the artcileGeneration of Hydrogen from Water: A Pd-Catalyzed Reduction of Water Using Diboron Reagent at Ambient Conditions, Application In Synthesis of 25240-59-9, the publication is Organic Letters (2016), 18(19), 5062-5065, database is CAplus and MEDLINE.

Production of hydrogen from renewable sources, particularly from water, is an intensive area of research, which has far-reaching relevance in hydrogen economy. A homogeneous catalytic method is presented for producing clean hydrogen gas from water, in a reaction of water with a diboron compound as the reductant, under ambient reaction conditions. The Pd-catalytic system is stable in water and displays excellent recyclability. Hydroxy analogs such as alcs. are compatible with the Pd/B₂Pin₂ system and generate hydrogen gas efficiently. The B₂Pin₂-H₂O system, in the presence of palladium, is an excellent catalytic system for selective hydrogenation of olefins.

Organic Letters published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Application In Synthesis of 25240-59-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bettinger, Holger F. published the artcileMetal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene, Synthetic Route of 25240-59-9, the publication is Angewandte Chemie, International Edition (2008), 47(25), 4744-4747, database is CAplus and MEDLINE.

C-H insertion: Borylnitrenes, which were generated in situ by photolysis of azides, convert unactivated alkanes by intermol. C-H insertion into aminoboranes, which in turn can be reacted further to give amines or amides. The boryl group serves two purposes: it converts the nitrene into a highly reactive BN vinylidene analog, and it is easily cleaved from the product. Caution: B azides may be explosive, and appropriate precautions must be taken when handling these compounds To study the reaction of catechol borylnitrene (C₆H₄O₂BN:, 1a) with methane, the authors isolated 2-azido-1,3,2-benzodioxaborole (C₆H₄O₂BN₃, 3a) in Ar doped with methane (1-2% CH₄ or CD₄) at 10 K. Photolysis of 3a using UV irradiation resulted in the complete disappearance of 3a, the concomitant formation of nitrene C₆H₄O₂BN: (1a) and of aminoborane C₆H₄O₂BN(H)Me (2a) according to IR spectra and DFT calculations of vibrational modes. Reaction of trimethylsilyl azide and 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolboron chloride (pinBCl)) gave 2-azido-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3b, pinacolboron azide (pinBN₃)) in 96% yield. Photolysis of 3b in cycloalkane solutions at room temperature afforded the expected aminoboranes pinBN(H)R (R = cyclopentyl, cyclohexyl, cycloheptyl) in 79% to 85% yield. The aminoboranes can conveniently be transformed into the corresponding primary amines or amides by alcoholysis or acylation, resp. The mol. structures of pinBN(H)R (R = cyclopentyl, cyclohexyl) were determined by x-ray crystallog.

Angewandte Chemie, International Edition published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Synthetic Route of 25240-59-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bolano, Tamara published the artcileAn Acyl-NHC Osmium Cooperative System: Coordination of Small Molecules and Heterolytic B-H and O-H Bond Activation, Name: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, the publication is Organometallics (2015), 34(15), 3902-3908, database is CAplus.

The hexahydride complex OsH₆(PⁱPr₃)₂ (1) activates the C-OMe bond of 1-(2-methoxy-2-oxoethyl)-3-methylimidazolium chloride (2), in addition to promoting the direct metalation of the imidazolium group, to afford a five-coordinate OsCl(acyl-NHC)(PⁱPr₃)₂ (3) compound The latter coordinates carbon monoxide, oxygen, and mol. hydrogen to give the corresponding carbonyl (4), dioxygen (5), and dihydrogen (6) derivatives Complex 3 also promotes the heterolytic bond activation of pinacolborane (HBpin), using the acyl oxygen atom as a pendant Lewis base. The hydride ligand and the Bpin substituent of the Fischer-type carbene of the resulting complex 7 activate the O-H bond of alcs. and water. As a consequence, complex 3 is a metal ligand cooperating catalyst for the generation of mol. hydrogen, by both the alcoholysis and hydrolysis of pinacolborane, via the intermediates 7 and 6.

Organometallics published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Name: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kuduk, Scott D. published the artcileDevelopment of Orally Bioavailable and CNS Penetrant Biphenylaminocyclopropane Carboxamide Bradykinin B₁ Receptor Antagonists, Product Details of C6H13BO3, the publication is Journal of Medicinal Chemistry (2007), 50(2), 272-282, database is CAplus and MEDLINE.

A series of biphenylaminocyclopropane carboxamide based bradykinin B₁ receptor antagonists has been developed that possesses good pharmacokinetic properties and is CNS penetrant. Discovery that the replacement of the trifluoropropionamide in the lead structure with polyhaloacetamides, particularly a trifluoroacetamide, significantly reduced P-glycoprotein mediated efflux for the series proved essential. One of these novel bradykinin B₁ antagonists (13b) also exhibited suitable pharmacokinetic properties and efficient ex vivo receptor occupancy for further development as a novel approach for the treatment of pain and inflammation.

Journal of Medicinal Chemistry published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Product Details of C6H13BO3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Viger, Mathieu L. published the artcileDistinct ON/OFF fluorescence signals from dual-responsive activatable nanoprobes allows detection of inflammation with improved contrast, Safety of 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, the publication is Biomaterials (2017), 119-131, database is CAplus and MEDLINE.

Visualization of biochem. changes associated with disease is of great clin. significance, as it should allow earlier, more accurate diagnosis than structural imaging, facilitating timely clin. intervention. Herein, we report combining stimuli-responsive polymers and near-IR fluorescent dyes (emission max: 790 nm) to create robust activatable fluorescent nanoprobes capable of simultaneously detecting acidosis and oxidative stress associated with inflammatory microenvironments. The spectrally-resolved mechanism of fluorescence activation allows removal of unwanted background signal (up to 20-fold reduction) and isolation of a pure activated signal, which enables sensitive and unambiguous localization of inflamed areas; target-to-background ratios reach 22 as early as 3 h post-injection. This new detection platform could have significant clin. impact in early detection of pathologies, individual tailoring of drug therapy, and image-guided tumor resection.

Biomaterials published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C17H14N2O2, Safety of 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Lyons, Amanda Jane published the artcileScaling up a C-H Borylation: Addressing the Safety Concerns of an Iridium-Catalyzed Process for Multikilo Scale Manufacture, Category: alcohols-buliding-blocks, the publication is Organic Process Research & Development (2022), 26(5), 1378-1388, database is CAplus.

Ir-catalyzed C-H borylation reactions are a rapid and versatile entry into Suzuki coupling partners, but their inherent safety issues can limit their use in large-scale manufacture The stoichiometric byproduct from this reaction, HBpin, can liberate H gas on contact with moisture in air, as well as acting as an effective borylating agent in the reaction, resulting in an addnl. pathway for the generation of H. Using a targeted, multidisciplinary approach, a C-H borylation process to generate a key intermediate in the synthesis of an API was redesigned in preparation for large-scale manufacture Through careful evaluation of the existing process and the use of high-throughput experimentation, PAT techniques, NMR, process safety experimentation, and process engineering, the process was constructed so that inherent risks associated with this reaction were minimized and contained to a final controlled quench of the reactive byproducts of the reaction. The final process was transferred to a manufacturing facility, delivering >70 kg of the borylated product over two batches.

Organic Process Research & Development published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Cao, Sheng published the artcileSubstituent Effects on Oxidation-Induced Formation of Quinone Methides from Arylboronic Ester Precursors, Application In Synthesis of 25240-59-9, the publication is Chemistry – A European Journal (2013), 19(27), 9050-9058, database is CAplus and MEDLINE.

A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N⁺Me₃Br^–) have been synthesized. The substituent effects on their reactivity with H₂O₂ and formation of quinone methide (QM) have been investigated. NMR spectroscopy and Et vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, resp. QMs were not generated during oxidative cleavage of the boronic esters but by subsequent transformation of the phenol products under physiol. conditions. The oxidative deboronation is facilitated by electron-withdrawing substituents, such as aromatic F, NO₂, or benzylic N⁺Me₃Br^–, whereas electron-donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH₃ or OMe group, or a good leaving group (Br), efficiently generate QMs under physiol. conditions. Finally, a quant. relationship between the structure and activity has been established for the arylboronic esters by using a Hammett plot. The reactivity of the arylboronic acids/esters and the inhibition or facilitation of QM formation can now be predictably adjusted. This adjustment is important as some applications may benefit and others may be limited by QM generation.

Chemistry – A European Journal published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Application In Synthesis of 25240-59-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhang, Tianhui published the artcileSynthesis of a phenylboronic ester-linked PEG-lipid conjugate for ROS-responsive drug delivery, Computed Properties of 25240-59-9, the publication is Polymer Chemistry (2017), 8(40), 6209-6216, database is CAplus.

Stimuli-responsive drug delivery systems (DDSs) offering spatial-temporal and dosage controlled transport of drugs in vivo have attracted much attention for anticancer drug delivery. In the present work, a kind of phenylboronic ester-linked PEG-lipid conjugate was designed and synthesized for H₂O₂-responsive drug delivery. Firstly, a chain-end alkynyl functionalized methoxy poly(ethylene glycol) with a phenylboronic pinacol ester linker was synthesized via a classical Passerini reaction of carboxyl functionalized methoxy poly(ethylene glycol)₂₀₀₀ (mPEG_2k-COOH), 4-formylphenylboronic pinacol ester and propargyl isocyanoacetamide. The obtained polymer was denoted as mPEG_2k-PBPE-alkynyl. Then, the oxidation-responsive cleavage of the phenylboronic pinacol ester linker between the mPEG_2k-COOH and alkynyl chain-end was verified by in situ¹H NMR and mass spectra characterization. Furthermore, the amphiphilic PEG-lipid conjugate was synthesized by the Cu(I)-catalyzed click reaction of mPEG_2k-PBPE-alkynyl and 3-azido-1,2-propanediol distearate (N₃-DSA). The resultant mPEG_2k-PBPE-DSA could self-assemble into stable micelles in aqueous media. Nile red was used as the model drug and was loaded into the micelles. The obtained drug loaded micelles exhibited a typical H₂O₂-responsive drug release behavior and could be effectively internalized by MCF-7 cells. In addition, the synthesized mPEG_2k-PBPE-DSA was tested to be nontoxic towards RAW264.7 cells. Therefore, this biocompatible mPEG_2k-PBPE-DSA conjugate would be promising for applications in ROS-responsive drug delivery.

Polymer Chemistry published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C10H10O2, Computed Properties of 25240-59-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts