1256355-30-2

Usage

Uses

Used in Pharmaceutical Synthesis:
5-Fluoro-2-formylphenylboronic acid is utilized as a key intermediate in the development of various pharmaceuticals. Its ability to be easily manipulated and modified allows for the creation of complex molecular structures that can target specific biological pathways, potentially leading to the discovery of new drugs with improved efficacy and selectivity.
Used in Agrochemical Development:
In the agrochemical industry, 5-Fluoro-2-formylphenylboronic acid is employed as a building block for the synthesis of novel compounds with pesticidal or herbicidal properties. Its unique reactivity and structure enable the design of molecules that can effectively control pests and weeds, contributing to increased crop yields and agricultural productivity.
Used in the Synthesis of Functional Materials:
5-Fluoro-2-formylphenylboronic acid is also used in the development of functional materials with specific properties, such as conductivity, magnetism, or optical activity. Its incorporation into these materials can lead to the creation of advanced materials for use in various applications, including electronics, sensors, and energy storage devices.
Used in Organic Synthesis as a Building Block:
5-Fluoro-2-formylphenylboronic acid is employed as a versatile building block in organic synthesis. Its boronic acid functional group allows for a wide range of reactions, enabling the construction of complex organic molecules with diverse applications in various industries, such as pharmaceuticals, materials science, and agrochemicals.
Used in Medicinal Chemistry for Structure-Activity Relationship Studies:
In medicinal chemistry, 5-Fluoro-2-formylphenylboronic acid is used to explore the structure-activity relationships of potential drug candidates. By incorporating 5-Fluoro-2-formylphenylboronic acid into various molecular frameworks, researchers can investigate the effects of structural modifications on biological activity, leading to the optimization of drug candidates for improved potency, selectivity, and safety.

InChI:InChI=1/C15H3F29O5/c16-2(1-45,7(22,23)24)46-13(39,40)4(19,9(28,29)30)48-15(43,44)6(21,11(34,35)36)49-14(41,42)5(20,10(31,32)33)47-12(37,38)3(17,18)8(25,26)27/h45H,1H2

Upstream product

• 40138-16-7 2-formylbenzene boronic acid 
• 1844839-22-0 4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 121-43-7 Trimethyl borate 
• 1239518-71-8 2-bromo-4-fluorobenzaldehyde dimethyl acetal 
• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 150-46-9 triethyl borate 

Relevant academic research and scientific papers

A simple quantitative chiral analysis of amino acid esters by fluorine-19 nuclear magnetic resonance using the modified James–Bull method

A simple chiral analysis of amino acid esters by fluorine-19 nuclear magnetic resonance (19F?NMR) through the modified James–Bull method is described. Thus, amino acid ester acid salt was treated with 5-fluoro-2-formylphenylboronic acid and (S)-BINOL in the presence of triethylamine (TEA) and MS4A for 10?minutes. The reaction mixture was analysed by 19F?NMR directly to afford good quantifications.

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

The production of β-lactamases represents the main cause of resistance to clinically important β-lactam antibiotics. Boron containing compounds have been demonstrated as promising broad-spectrum β-lactamase inhibitors to combat β-lactam resistance. Here we report a series of 3-aryl substituted benzoxaborole derivatives, which manifested broad-spectrum inhibition to representative serine-β-lactamases (SBLs) and metallo-β-lactamases (MBLs). The most potent inhibitor 9f displayed an IC50 value of 86 nM to KPC-2 SBL and micromolar inhibitory activity towards other tested enzymes. Cell-based assays further revealed that 9f was able to significantly reduce the MICs of meropenem in clinically isolated KPC-2-producing bacterial strains and it showed no apparent toxicity in HEK293T cells.

Design and enantioselective synthesis of 3-(α-acrylic acid) benzoxaboroles to combat carbapenemase resistance

Chiral 3-substituted benzoxaboroles were designed as carbapenemase inhibitors and efficiently synthesisedviaasymmetric Morita-Baylis-Hillman reaction. Some of the benzoxaboroles were potent inhibitors of clinically relevant carbapenemases and restored the activity of meropenem in bacteria harbouring these enzymes. Crystallographic analyses validate the proposed mechanism of binding to carbapenemases,i.e.in a manner relating to their antibiotic substrates. The results illustrate how combining a structure-based design approach with asymmetric catalysis can efficiently lead to potent β-lactamase inhibitors and provide a starting point to develop drugs combatting carbapenemases.

Lewis or Br?nsted? A Rectification of the Acidic and Aromatic Nature of Boranol-Containing Naphthoid Heterocycles

Boron-containing heterocycles are important in a variety of applications from drug discovery to materials science; therefore a clear understanding of their structure and reactivity is desirable to optimize these functions. Although the boranol (B-OH) unit of boronic acids behaves as a Lewis acid to form a tetravalent trihydroxyborate conjugate base, it has been proposed that pseudoaromatic hemiboronic acids may possess sufficient aromatic character to act as Br?nsted acids and form a boron oxy conjugate base, thereby avoiding the disruption of ring aromaticity that would occur with a tetravalent boronate anion. Until now no firm evidence existed to ascertain the structure of the conjugate base and the aromatic character of the boron-containing ring of hemiboronic "naphthoid"isosteres. Here, these questions are addressed with a combination of experimental, spectroscopic, X-ray crystallographic, and computational studies of a series of model benzoxazaborine and benzodiazaborine naphthoids. Although these hemiboronic heterocycles are unambiguously shown to behave as Lewis acids in aqueous solutions, boraza derivatives possess partial aromaticity provided their nitrogen lone electron pair is sufficiently available to participate in extended delocalization. As demonstrated by dynamic exchange and crossover experiments, these heterocycles are stable in neutral aqueous medium, and their measured pKa values are consistent with the ability of the endocyclic heteroatom substituent to stabilize a partial negative charge in the conjugate base. Altogether, this study corrects previous inaccuracies and provides conclusions regarding the properties of these compounds that are important toward the methodical application of hemiboronic and other boron heterocycles in catalysis, bioconjugation, and medicinal chemistry.

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

A sustainable catalyst- and solvent-free Passerini-tetrazole three component reaction (PT-3CR) has been developed for the selective synthesis of benzoxaborol-tetrazoles for the first time. The synthetic potential of oxaboroles was demonstrated towards various functionalized tetrazoles, which are otherwise difficult to achieve through conventional PT-3CR from aromatic aldehydes/ketones. The reaction features high practicality, broad substrate scope and excellent yields (80-98%). Preliminary results of the asymmetric PT-3CR are also shown for the synthesis of chiral benzoxaboroles.

A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by 1H and 19F NMR Spectroscopy

A practically simple three-component chiral derivatization protocol has been developed to determine the enantiopurity of eight S-chiral sulfinamides by 1H and 19F NMR spectroscopic analysis, based on their treatment with a 2-formylphenylboronic acid template and enantiopure pinanediol to afford a mixture of diastereomeric sulfiniminoboronate esters whose diastereomeric ratio is an accurate reflection of the enantiopurity of the parent sulfinamide.

Fluoro-substituted 2-formylphenylboronic acids: Structures, properties and tautomeric equilibria

Four isomeric fluoro-2-formylphenylboronic acids were synthesized and characterized by 1H, 13C, 19F and 17O NMR. Molecular and crystal structure of two compounds was determined by single crystal XRD method. pKa values of all the isomers have been determined by spectrophotometric method and compared with the results for the corresponding benzoxaboroles as well as fluoro- and formylphenylboronic acids. Tautomeric equilibrium with cyclic benzoxaborole form was investigated. The influence of position of fluorine substituents on the properties of investigated compounds is discussed.