356570-52-0

Usage

Uses

Used in Organic Synthesis:
4-METHYLBENZYLBORONIC ACID PINACOL ESTER is used as a reagent for its ability to participate in various organic reactions, facilitating the formation of new chemical bonds and structures.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
In the field of organic chemistry, 4-METHYLBENZYLBORONIC ACID PINACOL ESTER is utilized as a key component in Suzuki-Miyaura cross-coupling reactions. These reactions are significant for the formation of carbon-carbon bonds, which are crucial in constructing complex organic molecules, including pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
4-METHYLBENZYLBORONIC ACID PINACOL ESTER is used as an intermediate in the synthesis of pharmaceutical compounds. Its reactivity and stability make it suitable for creating molecules with specific therapeutic properties.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 4-METHYLBENZYLBORONIC ACID PINACOL ESTER is employed as an intermediate in the development of agrochemical products, such as pesticides and herbicides, where its ability to form stable and reactive compounds is advantageous.
Used in Research and Development:
4-METHYLBENZYLBORONIC ACID PINACOL ESTER is also used in research and development settings as a tool to explore new reaction pathways and to develop innovative synthetic methods in organic chemistry.

InChI:InChI=1/C14H21BO2/c1-11-6-8-12(9-7-11)10-15-16-13(2,3)14(4,5)17-15/h6-9H,10H2,1-5H3

Upstream product

• 104-81-4 4-Methylbenzyl bromide 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 2216-45-7 p-methylbenzyl alcohol acetate 
• 73183-34-3 bis(pinacol)diborane 
• 106-42-3 para-xylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 5720-05-8 4-methylphenylboronic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 589-18-4 4-Methylbenzyl alcohol 
• 29540-83-8 p-tolyl triflate 
• 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 
• 4052-88-4 4-methyl-N,N-dimethylbenzylamine 
• 106-38-7 para-bromotoluene 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 622-96-8 4-methylethylbenzene 
• 589-18-4 4-Methylbenzyl alcohol 
• 622-47-9 4-tolylacetic acid 
• 1041810-08-5 1-(4-chlorophenyl)-2-(p-tolyl)ethan-1-ol 
• 103094-49-1 5-(p-tolyl)pentan-2-one 
• 1173167-10-6 (1S)-1-chloro-2-(4-methylbenzyl)boronic acid (+)-pinanediol ester 
• 1457967-21-3 N⁴-benzyl-6-(4-methylbenzyl)-3-nitro-N²-(2,4,4-trimethylpentan-2-yl)pyridine-2,4-diamine 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 62849-46-1 N-benzyl-4-methoxy-N-(4-methylbenzyl)aniline 
• 16547-09-4 N-methyl-N-(4-methylbenzyl)aniline 
• 1373432-92-8 C₂₈H₃₁N₃O₃ 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Relevant academic research and scientific papers

Iridium-Catalyzed sp3 C-H Borylation in Hydrocarbon Solvent Enabled by 2,2′-Dipyridylarylmethane Ligands

Iridium-catalyzed alkane C-H borylation has long suffered from poor atom economy, resulting from both the inclusion of only 1 equiv of boron from the diboron reagent and a requirement for neat substrate. An appropriately substituted dipyridylarylmethane ligand was found to give highly active alkane borylation catalysts that facilitate C-H borylation with improved efficiency. This system provides for complete consumption of the diboron reagent, producing 2 molar equivalents of product at low catalyst loadings. The superior efficacy of this system also enables borylation of unactivated alkanes in hydrocarbon solvent with a reduced excess of substrate and improved functional group compatibility. The effectiveness of this ligand is displayed across a selection of functional groups, both under traditional borylation conditions in neat substrate and under atypical conditions in cyclohexane solvent. The utility of this catalytic system is exemplified by the borylation of substrates containing polar functionality, which are unreactive toward C-H borylation under neat conditions.

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

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.

(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

Visible-light-driven graphene supported Cu/Pd alloy nanoparticle-catalyzed borylation of alkyl bromides and chlorides in air

A highly efficient photocatalytic protocol for borylation of alkyl bromides and chlorides with graphene supported Cu/Pd alloy nanoparticles as a heterogeneous catalyst is reported. This photocatalytic system operates with visible light in air, providing a wide range of primary and secondary alkyl halides with B2pin2 or B2neop2 in high yields at low temperatures, thereby demonstrating its broad utility and functional group tolerance. The high performance is attributed to a synergistic effect of localized surface plasmon resonance (LSPR) of Cu and charge transfer from Cu to Pd due to the alloy surface charge heterogeneity. Transfer of energetic electrons from Pd to electrophilic alkyl halides lead to the formation of the alkyl radicals, which quickly react with a nucleophilic adduct of a diboron compound with base adsorbed on the positively charged Cu sites to form the corresponding borylation product.

Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i)

Proteasomes are broadly expressed key components of the ubiquitin-dependent protein degradation pathway containing catalytically active subunits (β1, β2, and β5). LMP7 (β5i) is a subunit of the immunoproteasome, an inducible isoform that is predominantly expressed in hematopoietic cells. Clinically effective pan-proteasome inhibitors for the treatment of multiple myeloma (MM) nonselectively target LMP7 and other subunits of the constitutive proteasome and immunoproteasome with comparable potency, which can limit the therapeutic applicability of these drugs. Here, we describe the discovery and structure-based hit optimization of novel amido boronic acids, which selectively inhibit LMP7 while sparing all other subunits. The exploitation of structural differences between the proteasome subunits culminated in the identification of the highly potent, exquisitely selective, and orally available LMP7 inhibitor 50 (M3258). Based on the strong antitumor activity observed with M3258 in MM models and a favorable preclinical data package, a phase I clinical trial was initiated in relapsed/refractory MM patients.

Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones

Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same deoxygenation manifold with aliphatic aldehydes and ketones, we also enable a concise synthesis of 1,1,2-tris(boronates), a family of compounds that currently lack efficient synthetic methods. Given its simplicity and versatility, we expect that this novel borylation approach could show great promise in organoboron synthesis and inspire more carbonyl deoxygenative transformations in both academic and industrial settings.

Efficient synthesis of alkylboronic esters: Via magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides

We report a magnetically separable Cu nanocatalyst (Fe-DOPA-Cu) for the borylation of alkyl halides with alkoxy diboron reagents, providing alkylboronic esters in high yields, with broad functional group tolerance under mild reaction conditions. The procedure is also applicable to the borylation of benzyl chlorides and bromides. Radical clock experiments support a radical-mediated process. Easy recycling of the catalyst resulted in no significant loss of activity up to ten runs.

Regioselective α-benzylation of 3-iodoazetidine via Suzuki cross-coupling

An efficient protocol for the synthesis of α-benzyl azetidines starting from benzylboronic acid pinacol ester derivatives and 3-iodoazetidine was developed. A wide range of α-benzyl azetidine derivatives were obtained in moderate to good yields with high regioselectivity (>99%).