710348-63-3

Usage

Uses

Used in Organic Synthesis:
3-(METHYLTHIO)PHENYLBORONIC ACID PINACOLATE is used as a reagent in organic synthesis for cross-coupling reactions to form carbon-carbon bonds. Its ability to participate in these reactions contributes to the creation of complex organic molecules.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, 3-(METHYLTHIO)PHENYLBORONIC ACID PINACOLATE is used as a building block for the preparation of various pharmaceuticals. Its structural features allow it to be incorporated into the synthesis of drug molecules, potentially leading to new therapeutic agents.
Used in Agrochemical Development:
3-(METHYLTHIO)PHENYLBORONIC ACID PINACOLATE is also utilized in the development of agrochemicals, serving as a key component in the synthesis of compounds designed to protect crops and enhance agricultural productivity.
Used in Materials Science:
3-(METHYLTHIO)PHENYLBORONIC ACID PINACOLATE has applications in materials science, where it can be used to develop new materials with specific properties, such as improved conductivity or stability.
Used in Chemical Biology Research and Drug Discovery:
3-(METHYLTHIO)PHENYLBORONIC ACID PINACOLATE has shown potential as a tool in chemical biology research and drug discovery due to its ability to selectively bind to specific biological targets. This selective binding property makes it a valuable probe for studying biological systems and identifying new therapeutic leads.

InChI:InChI=1/C13H21BO3S/c1-12(2,15)13(3,4)17-14(16)10-7-6-8-11(9-10)18-5/h6-9,15-16H,1-5H3

Upstream product

• 4867-37-2 1-chloro-3-methylsulfanylbenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 100-68-5 methyl-phenyl-thioether 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 144458-60-6 2,2,2-trifluoro-N-(3-(methylthio)phenyl)acetamide 

Relevant academic research and scientific papers

Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand

A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.

Lewis Acid–Base Interaction-Controlled ortho-Selective C?H Borylation of Aryl Sulfides

An iridium/bipyridine-catalyzed ortho-selective C?H borylation of aryl sulfides was developed. High ortho-selectivity was achieved by a Lewis acid–base interaction between a boryl group of the ligand and a sulfur atom of the substrate. This is the first example of a catalytic and regioselective C?H transformation controlled by a Lewis acid–base interaction between a ligand and a substrate. The C?H borylation reaction could be conducted on a gram scale, and with a bioactive molecule as a substrate, demonstrating its applicability to late-stage regioselective C?H borylation. A bioactive molecule was synthesized from an ortho-borylated product by converting the boryl and methylthio groups of the product.

METHOD FOR PREPARING AMINOARYLBORANE COMPOUNDS OR DERIVATIVES THEREOF

The present invention provides a process for the preparation of aminoarylborane compounds and derivatives thereof comprising a step of arylation by reacting an aryl chloride with an aminoborane compound in the presence of a catalytic system.

Method for preparing aminoarylborane compounds or derivatives thereof

The present invention provides a process for the preparation of aminoarylborane compounds and derivatives thereof comprising a step of arylation by reacting an aryl chloride with an aminoborane compound in the presence of a catalytic system. Typically, th

Borylation of unactivated aryl chlorides under mild conditions by using diisopropylaminoborane as a borylating reagent

The synthesis of arylboronic ester derivatives from aryl chlorides by using aryl(amino)boranes is described. Palladium-catalyzed coupling between aryl chlorides and diisopropylaminoborane leads to the formation of a C-B bond under mild conditions. A wide range of functional groups are tolerated, making this method particularly useful for the borylation of functionalized aromatics. Salts make the difference: The synthesis of arylboronic ester derivatives from aryl chlorides by using aryl(amino)boranes is described. Palladium-catalyzed coupling between aryl chlorides and diisopropylaminoborane leads to the formation of a C-B bond under mild conditions. A wide range of substituents, including electron-withdrawing groups, are tolerated (see scheme).