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Usage

Uses

Used in Organic Synthesis:
2-Fluoro-3-hydroxymethylphenylboronic acid is used as a reagent in organic synthesis for the formation of carbon-carbon and carbon-heteroatom bonds. Its application is primarily through the Suzuki-Miyaura coupling reaction, a widely used method for the formation of carbon-carbon bonds, which is crucial for the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Fluoro-3-hydroxymethylphenylboronic acid is utilized as a key intermediate in the preparation of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Agrochemicals:
2-Fluoro-3-hydroxymethylphenylboronic acid also finds application in the agrochemical sector, where it serves as a building block for the synthesis of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in crop protection and pest management.
Used in Material Science:
With its potential applications in the development of new materials, 2-Fluoro-3-hydroxymethylphenylboronic acid is used as a component in the synthesis of various functionalized organic compounds. Its unique properties can contribute to the creation of materials with specific characteristics, such as improved stability or reactivity, for use in various industries.
Overall, 2-Fluoro-3-hydroxymethylphenylboronic acid is a versatile chemical compound with applications spanning across multiple industries, including organic synthesis, pharmaceuticals, agrochemicals, and material science. Its unique structure and reactivity make it a valuable asset in the development of new compounds and materials with diverse applications.

Upstream product

• 849061-98-9 (2-fluoro-3-formylphenyl)boronic acid 

Relevant academic research and scientific papers

An intramolecular: Ortho -assisted activation of the silicon-hydrogen bond in arylsilanes: An experimental and theoretical study

An intramolecular activation of the Si-H bond in arylsilanes by selected ortho-assisting functional groups based on boron, carbon and phosphorus was investigated experimentally and by means of theoretical calculations. The major conclusion drawn is that the presence of a negatively charged oxygen atom in the functional group is essential for providing effective chelation to the silicon atom which in turn results in the increased hydridic character of a resulting five-coordinated species. In contrast, an intermolecular attack of hydroxide on the silicon atom in aryldimethylsilane results in the activation of the silicon-aryl bond. This increased reactivity of the Si-H bond in intramolecularly coordinated arylsilanes can be ascribed to a significant trans effect which operates in the preferred configuration. Hydrolytic cleavage of the Si-H bond results in dihydrogen elimination and the formation of various silicon heterocyclic systems such as benzosiloxaboroles, spiro-bis(siloxa)borinate, benzosilalactone and benzophosphoxasilole. In addition, intermolecular reduction of benzaldehydes with ortho-boronated arylsilane was observed whereas compounds bearing other reducible functional groups (COMe, COOEt, CN and NO2) were inert under comparable conditions. Specifically, an intramolecular reduction of the CN group in an ortho-silylated benzonitrile derivative was observed. The mechanism of Si-H bond activation was investigated by the DFT theoretical calculations. The calculations showed that the intramolecular coordination of the silicon atom effectively prevents the cleavage of the Si-aryl bond. Furthermore, the reaction is favored in anionic systems bearing COO-, B(OH)3- or CH2O- groups, while in the case of neutral functional groups such as PO(OEt)2 the process is much slower.