269409-70-3

Usage

Uses

Used in Chemical Synthesis:
4-Hydroxyphenylboronic acid pinacol ester is used as a reagent in chemical synthesis for its ability to participate in various organic reactions, including the formation of carbon-carbon bonds.
Used in Suzuki Coupling Chemistry:
In the field of organic chemistry, 4-Hydroxyphenylboronic acid pinacol ester is used as a key component in Suzuki coupling reactions, which are widely employed for the formation of biaryl compounds. These reactions are significant in the synthesis of pharmaceuticals, agrochemicals, and advanced materials.
Used in the Pharmaceutical Industry:
4-Hydroxyphenylboronic acid pinacol ester is utilized as an intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in the Synthesis of Advanced Materials:
4-Hydroxyphenylboronic acid pinacol ester is also used as a building block in the creation of advanced materials, such as organic semiconductors and optoelectronic devices, due to its ability to form stable and functional molecular structures.

InChI:InChI=1/C12H17BO3/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8,14H,1-4H3

Upstream product

• 540-38-5 p-Iodophenol 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 106-48-9 4-chloro-phenol 
• 73183-34-3 bis(pinacol)diborane 
• 17878-44-3 (4-bromophenoxy)trimethylsilane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 106-41-2 4-bromo-phenol 
• 123-30-8 4-amino-phenol 
• 1073-72-9 4-hydroxythioanisole 
• 480438-75-3 t-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate 
• 1415236-88-2 2-(4-(allyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 108-95-2 phenol 
• 61807-37-2 benzoic acid 4‐iodophenyl ester 

Downstream Products

• 854371-73-6 3-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenoxymethyl]benzofuran 
• 452343-10-1 2-(4-hydroxyphenyl)-4-(3-pyridin-2-yl-1-trityl-1H-pyrazol-4-yl)pyridine 
• 1020576-09-3 3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole 
• 769968-17-4 tert-butyl 2-(4-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate 
• 3916-44-7 4-(4-nitrophenyl)phenol 
• 16881-71-3 4'-methoxy-1,1'-biphenyl-4-ol 
• 701271-51-4 4-[6-(4-hydroxy-phenyl)-pyridine-3-sulfonyl]-tetrahydro-pyran-4-carboxylic acid tert-butyl ester 
• 656257-47-5 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetamide 
• 474694-39-8 4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenol 
• 657398-80-6 4-{4-[3-(6-methylpyridin-2-yl)-1-trityl-1h-pyrazol-4-yl]pyridin-2-yl-}phenol 
• 656257-49-7 1-[(morpholin-4-yl)-carbonylmethyloxy]-4-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]-benzene 
• 690636-28-3 4-(2-( 4-( 4, 4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)morpholine 
• 269410-28-8 ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate 
• 185413-64-3 5,5'-bis(4-hydroxyphenyl)-2,2'-bithiophene 

Relevant academic research and scientific papers

One-pot synthesis of Ag-Cu-Cu2O/C nanocomposites derived from a metal-organic framework as a photocatalyst for borylation of aryl halide

Mixed metal-metal oxide/C (Ag-Cu-Cu2O/C) nanocomposites were synthesized by the heat treatment of a metal-organic framework under a N2 flow using the one-pot synthesis method. The as-prepared nanocomposites were characterized using a range of techniques,

Computational and Synthetic approach with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S triple mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)

New substituted quinoline derivatives were designed and synthesized via a five-step modified Suzuki coupling reaction. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. All docking studies confirmed high potency and flexibility towards wild type as well as a mutated enzyme. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M/C797S and L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Most of the quinoline derivatives revealed a significant cytotoxic effect. The IC50 values of 4-(4-methylquinolin-2-yl)phenyl 4-(chloromethyl)benzoate (5j) were found to be 0.0042 μM, 0.02 μM, 1.91 μM, 3.82 μM and 3.67 μM while IC50 values of osimertinib were 0.0040 μM, 0.02 μM, ND, 0.99 μM and 1.22 μM, respectively. Compound 5j has shown excellent inhibitory activities against EGFR kinases triple mutant with IC 50 value 1.91 μM. It was observed that, compared to H1975, A549 and A431 cell lines, synthesized compounds significantly inhibited proliferation of the HCC827 cell line. These data suggested that synthesized compounds showed promising selective anticancer activity against tumor cells harboring EGFR Del E746-A750. The potency of compound 5j was compared through molecular dynamic simulations and an insilico ADMET study. QSAR models were generated and the best model was correctly compared with respect to predicted and observed activity of compounds. The built model will assist to design, refine and construct novel substituted quinoline derivatives as potent EGFR inhibitors in near future.

Preparation method of aryl borate catalyzed by cesium neovalerate

The preparation method comprises the following steps: dissolving a compound of formula (I) and a diboron compound in an organic solvent, then adding an organic solvent dissolved with cesium neovalerate, palladium acetate and triphenylphosphine, and carrying out reaction to obtain aryl boronic acid ester. In the formula (I) R1. R2, R3, R4 and R5 are each independently selected from H, C. 1 - C10 Alkyl group, C2 - C10 Alkenyl, C2 - C10 Alkynyl group, C1 - C10 Alkoxy, hydroxy, hydroxy-substituted C1 - C10 Alkyl, phenyl, C1 - C10 Alkylamino. X Is selected from F, Cl, Br, i. The preparation method has the advantages of low production cost, high product yield, high purity, simple operation and suitability for industrial mass production.

Liquid crystal phosphorescent material based on cyclometalated complex and application thereof

The invention discloses a cyclometalated organic liquid crystal phosphorescent material based on 2-phenylpyridine as a main ligand and acetylacetone as an auxiliary ligand. A benzoic acid derivative liquid crystal unit is introduced into the main ligand 2

Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates

Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.

Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides

Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN?-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Improvement in the Palladium-Catalyzed Miyaura Borylation Reaction by Optimization of the Base: Scope and Mechanistic Study

Aryl boronic acids and esters are important building blocks in API synthesis. The palladium-catalyzed Suzuki-Miyaura borylation is the most common method for their preparation. This paper describes an improvement of the current reaction conditions. By using lipophilic bases such as potassium 2-ethyl hexanoate, the borylation reaction could be achieved at 35 °C in less than 2 h with very low palladium loading (0.5 mol %). A preliminary mechanistic study shows a hitherto unrecognized inhibitory effect by the carboxylate anion on the catalytic cycle, whereas 2-ethyl hexanoate minimizes this inhibitory effect. This improved methodology enables borylation of a wide range of substrates under mild conditions.

Photocatalytic C–X borylation of aryl halides by hierarchical SiC nanowire-supported Pd nanoparticles

Hierarchical SiC nanowire-supported Pd nanoparticles showed high photocatalytic activity for the C-X (X = Br, I) borylation of aryl halides at 30 °C. The SiC/Pd Mott-Schottky contact enhances the rapid transfer of the photogenerated electrons from SiC to the Pd nanoparticles. As a result, the concentrated energetic electrons in the Pd nanoparticles can facilitate the cleavage of C-I or C-Br bonds, which normally requires high-temperature thermal processes. We show that the present Pd/SiC photocatalyst is capable of catalyzing the transformation of a large variety of aryl halides to their corresponding boronate esters under visible light irradiation, with excellent yields.

Para-selective borylation of monosubstituted benzenes using a transient mediator

Herein, we conceptualized a transient mediator approach that has the capability of para-selective C-H functionalization of monosubstituted aromatics. This approach is enabled by in situ generation of a versatile sulfonium salt via highly electrophilic phenoxathiine or thianthrene dication intermediate which can be readily generated from its sulfoxide with trifluoromethanesulfonic anhydride. Preliminary mechanistic study implied that the remarkable para selectivity might be related to the incredible electrophilicity of thianthrene dication intermediate. The versatility of this approach was demonstrated via para-borylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.