243145-83-7

Basic information

• Product Name: 4-Fluorobenzylboronic acid pinacol ester
• Synonyms: 4-fluorobenzylboronic acid pinacol ester;2-(4-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Fluorobenzylboronic acid pinacol este;2-(4-Fluorobenzyl);2-[(4-fluorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 243145-83-7
• Molecular Formula: C₁₃H₁₈BFO₂
• Molecular Weight: 236.09
• Mol File: 243145-83-7.mol

Chemical Properties

• Boiling Point: 275 °C
• Flash Point: 120 °C
• Appearance: /
• Density: 1.04
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 4-Fluorobenzylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorobenzylboronic acid pinacol ester(243145-83-7)
• EPA Substance Registry System: 4-Fluorobenzylboronic acid pinacol ester(243145-83-7)

Safety Data

• Hazardous Substances Data: 243145-83-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Fluorobenzylboronic acid pinacol ester is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, which are critical in the synthesis of various organic compounds and pharmaceuticals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-Fluorobenzylboronic acid pinacol ester is utilized as a key intermediate in the development of new drugs, facilitating the creation of complex molecular structures that are otherwise challenging to synthesize.
Used in Pharmaceutical Chemistry:
4-Fluorobenzylboronic acid pinacol ester is employed as a building block in the pharmaceutical industry, contributing to the synthesis of active pharmaceutical ingredients and enhancing the efficiency of drug production processes.
Used in Material Science:
4-Fluorobenzylboronic acid pinacol ester is also used as a precursor in the development of new materials, where its unique properties can be leveraged to create innovative substances with specialized applications.
Used in Chemical Research:
4-Fluorobenzylboronic acid pinacol ester serves as a valuable tool in chemical research, particularly in the study of reaction mechanisms and the development of new synthetic methodologies.

Upstream product

• 459-46-1 4-Fluorobenzyl bromide 
• 73183-34-3 bis(pinacol)diborane 
• 352-32-9 p-fluorotoluene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 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 
• 459-57-4 4-fluorobenzaldehyde 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 702-11-4 4-fluoro-N,N-dimethylbenzylamine 
• 502-00-1 p-fluorobenzyl acetate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1765-93-1 4-fluoroboronic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 210422-66-5 4-fluorobenzaldehyde p-toluenesulfonylhydrazone 
• 17151-47-2 tributyl(4-fluorophenyl)stannane 

Downstream Products

• 457947-87-4 C₁₇H₁₂BrClFNO 
• 457947-95-4 C₁₈H₁₅BrFNO 
• 459-47-2 1-ethyl-4-fluorobenzene 
• 63416-76-2 5-(4-fluorophenyl)pentan-2-one 
• 1373432-89-3 C₂₇H₂₈FN₃O₃ 
• 405-50-5 p-Fluorophenylacetic acid 

Relevant articles and documents

A preparation of benzylic and allylic boronates: Cross-coupling of aryl- and alkenylstannanes with bromomethylboronates

Palladium catalyzed cross-coupling of aryl- or alkenylstannanes with pinacol and pinanediol bromomethylboronates affords the corresponding homologated benzylic or allylic boronates in moderate to good yields.

Synthesis of benzylic boronates via palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with benzylic halides

The palladium cross-coupling reaction of benzyl halides with diboron 1 yielded structurally diverse pinacol benzylic boronates. Under these reaction conditions, sensitive functionalities such as esters and nitriles are tolerated and the benzylic boronates

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.

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.

Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates

α-Haloboronates are useful organic synthons that can be converted to a diverse array of α-substituted alkyl borons. Methods to α-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C?Br bond in the brominated product could be readily transformed to a series of C?C, C?O, C?N, C?S, C?P, and C?I bonds, some of which are difficult to forge with α-halo sp2-B boronate esters. An activation effect of B(MIDA) moiety was found.

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.

IMMUNOPROTEASOME INHIBITORS

Provided herein are compounds, such as a compound of Formula (I), 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.

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%).

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.

Method for synthesizing alkylborate compound

The invention discloses a method for synthesizing an alkylborate compound, and concretely relates to a method for synthesizing the alkylborate compound through a cross-coupling reaction of chloralkaneand bis(pinacolato)diboron in the presence of metallic magnesium with Fe(acac)3 (acac = an acetylacetonate group) as a single component catalyst. The method for synthesizing the alkylborate compoundavoids the use of sensitive metal organic solvents and multi-component catalysts, realizes bilateral utilization of the bis(pinacolato)diboron, greatly reduces the use amount of the bis(pinacolato)diboron, and allows the coupling reaction of the cheap and easily-available chloralkane to be smoothly carried out under mild conditions; and compared with methods reported in literatures, the method disclosed in the invention has a better atom economy, a same or higher catalysis efficiency and a wider substrate applicability.