475250-52-3

Usage

Uses

Used in Organic Synthesis:
4-Methoxybenzylboronic acid pinacol ester is used as a reagent for the creation of functionalized benzene derivatives, leveraging its methoxy-substituted aromatic ring to enhance the synthesis of diverse organic compounds.
Used in Suzuki-Miyaura Coupling Reactions:
In the field of organic chemistry, 4-Methoxybenzylboronic acid pinacol ester serves as a key reagent in Suzuki-Miyaura coupling reactions, a prevalent method for the formation of carbon-carbon bonds. Its application in this reaction is instrumental in the synthesis of complex organic molecules, contributing to the development of pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
4-Methoxybenzylboronic acid pinacol ester is employed as an intermediate in the synthesis of pharmaceutical compounds, where its ability to form stable and reactive boron-containing intermediates is crucial for the development of new drugs with improved efficacy and selectivity.
Used in Materials Science:
In materials science, 4-Methoxybenzylboronic acid pinacol ester is utilized in the synthesis of novel materials with specific properties, such as conductivity, magnetism, or optical characteristics, by forming carbon-carbon bonds through Suzuki-Miyaura coupling reactions.
Used in Agrochemical Industry:
4-Methoxybenzylboronic acid pinacol ester is applied in the development of agrochemicals, where its role in creating complex organic molecules contributes to the design of new pesticides or herbicides with enhanced performance and selectivity for target organisms.

InChI:InChI=1/C14H23BO4/c1-13(2,16)14(3,4)19-15(17)10-11-6-8-12(18-5)9-7-11/h6-9,16-17H,10H2,1-5H3

Upstream product

• 70744-47-7 (p-methoxyphenyl)tri-n-butylstannane 
• 166330-03-6 pinacol (bromomethyl)boronate 
• 824-94-2 p-methoxybenzyl chloride 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 104-93-8 p-methylanizole 
• 2746-25-0 p-Methoxybenzyl bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 123-11-5 4-methoxy-benzaldehyde 
• 1416982-07-4 1-(4-methoxyphenyl)-N,N,N-trimethylmethanaminium trifluoromethanesulfonate 
• 15175-54-9 N,N-dimethyl-4-methoxylbenzylamine 
• 66107-29-7 4-methoxyphenyl triflate 

Downstream Products

• 42238-20-0 1-(4-methoxyphenyl)but-3-en-2-ol 
• 66265-99-4 5-(4-methoxyphenyl)pentan-2-one 
• 56047-51-9 4-(4-methoxyphenyl)butyraldehyde 
• 72457-25-1 4-(4-methoxyphenyl)butanenitrile 
• 20637-08-5 4-(4-methoxyphenyl)butyric acid methyl ester 
• 898785-44-9 3-(4-methoxybenzyl)cyclohexan-1-one 
• 56753-75-4 1-(4-Methoxyphenyl)-3-pyridin-4-ylpropan 
• 84289-40-7 3-(4-methoxybenzyl)-chroman-4-one 
• 105-13-5 4-Methoxybenzyl alcohol 

Relevant academic research and scientific papers

Selective Benzylic CH-Borylations by Tandem Cobalt Catalysis

Metal-catalyzed C?H activations are environmentally and economically attractive synthetic strategies for the construction of functional molecules as they obviate the need for pre-functionalized substrates and minimize waste generation. Great challenges reside in the control of selectivities, the utilization of unbiased hydrocarbons, and the operation of atom-economical dehydrocoupling mechanisms. An especially mild borylation of benzylic CH bonds was developed with the ligand-free pre-catalyst Co[N(SiMe3)2]2 and the bench-stable and inexpensive borylation reagent B2pin2 that produces H2 as the only by-product. A full set of kinetic, spectroscopic, and preparative mechanistic studies are indicative of a tandem catalysis mechanism of CH-borylation and dehydrocoupling via molecular CoI catalysts.

C(sp3)-H selective benzylic borylation by in situ reduced ultrasmall Ni species on CeO2

Herein, we report that highly dispersed Ni hydroxide species supported on CeO2 act as an efficient heterogeneous catalyst for the selective borylation of benzylic C(sp3)-H bonds of alkylarenes including secondary derivatives, using pinacolborane as the bo

(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors

(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, decharcogenative, and decarboxylative borylations proceeded in the presence of a radica

Practical Synthesis of Allyl, Allenyl, and Benzyl Boronates through SN1′-Type Borylation under Heterogeneous Gold Catalysis

Efficient borylation of sp3 C-O bonds by supported Au catalysts is described. Au nanoparticles supported on TiO2 showed high activity under mild conditions employing low catalyst loading conditions without the aid of any additives, such as phosphine and bases. A variety of allyl, propargyl, and benzyl substrates participated in the heterogeneously catalyzed reactions to furnish the corresponding allyl, allenyl, and benzyl boronates in high yields. Besides, Au/TiO2 was also effective for the direct borylation of allylic and benzylic alcohols. A mechanistic investigation based on a Hammett study and control experiments revealed that sp3 C-O bond borylation over supported Au catalysts proceeded through SN1′-type mechanism involving the formation of a carbocationic intermediate. The high activity, reusability, and environmental compatibility of the supported Au catalysts as well as the scalability of the reaction system enable the practical synthesis of valuable organoboron compounds.

Extremely facile formation of the pavine alkaloid skeleton by the photoreaction between isoquinoline and benzyltrifluoroborate

Appling the photo-benzylation of isoquinoline with benzyltrifluoroborate, an extremely facile method for the construction of a pavine alkaloid skeleton was developed. When 3-methoxybenzylboron reagents were employed to the reaction, it was found that not

Nickel-Catalyzed 1,1-Alkylboration of Electronically Unbiased Terminal Alkenes

An unprecedented nickel-catalyzed 1,1-alkylboration of electronically unbiased alkenes has been developed, providing straightforward access to secondary aliphatic boronic esters from readily available materials under very mild reaction conditions. The regioselectivity of this reaction is governed by a unique pyridyl carboxamide ligated catalyst, rather than the substrates. Moreover, this transformation shows excellent chemo- and regio-selectivity and remarkably good functional-group tolerance. We also demonstrate that under balloon pressure, ethylene can also be utilized as a substrate. Additionally, competence experiments indicate that selective bond formation is favored at the α-position of boron and preliminary mechanistic studies indicate that the key step in this three-component reaction involves a 1,2-nickel migration.

Deoxygenative Borylation of Secondary and Tertiary Alcohols

Two different approaches for the deoxygenative radical borylation of secondary and tertiary alcohols are presented. These transformations either proceed through a metal-free silyl-radical-mediated pathway or utilize visible-light photoredox catalysis. Readily available xanthates or methyl oxalates are used as radical precursors. The reactions show broad substrate scope and high functional-group tolerance, and are conducted under mild and practical conditions.

Rapid Assessment of the Reaction-Condition-Based Sensitivity of Chemical Transformations

A systematic, user-friendly assessment tool that delivers a clear overview of the sensitivity of reactions to key parameters is highly desirable. Herein, the development of such a method is described. The intuitive, standardized presentation of the result

Structure-based development of (1-(3′-Mercaptopropanamido)methyl)boronic Acid Derived Broad-Spectrum, Dual-Action Inhibitors of Metallo- And Serine-β-lactamases

The emergence and spread of bacterial pathogens acquired metallo-β-lactamase (MBL) and serine-β-lactamase (SBL) medicated β-lactam resistance gives rise to an urgent need for the development of new dual-action MBL/SBL inhibitors. Application of a pharmacophore fusion strategy led to the identification of (2′S)-(1-(3′-mercapto-2′-methylpropanamido)methyl)boronic acid (MS01) as a new dual-action inhibitor, which manifests broad-spectrum inhibition to representative MBL/SBL enzymes, including the widespread VIM-2 and KPC-2. Guided by the VIM-2:MS01 and KPC-2:MS01 complex structures, further structural optimization yielded new, more potent dual-action inhibitors. Selectivity studies indicated that the inhibitors had no apparent inhibition to human angiotensin-converting enzyme-2 and showed selectivity across serine hydrolyases in E. coli and human HEK293T cells labeled by the activity-based probe TAMRA-FP. Moreover, the inhibitors displayed potentiation of meropenem efficacy against MBL- or SBL-positive clinical isolates without apparent cytotoxicity. This work will aid efforts to develop new types of clinically useful dual-action inhibitors targeting MBL/SBL enzymes.

IMMUNOPROTEASOME INHIBITORS

Provided herein are compounds, such as a compound of Formula (I), as described herein, or a pharmaceutically acceptable salt thereof, that are immunoproteasome (such as LMP2 and LMP7) inhibitors. The compounds described herein can be useful for the treatment of diseases treatable by inhibition of immunoproteasomes. Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.