40276-63-9

Usage

Uses

Used in Organic Synthesis:
2-Benzylphenylboronic acid is used as a building block for the synthesis of various pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure allows it to be a key component in the creation of complex organic molecules, contributing to the development of new and improved products in these industries.
Used in the Suzuki-Miyaura Cross-Coupling Reaction:
In the field of organic chemistry, 2-benzylphenylboronic acid is utilized in the Suzuki-Miyaura cross-coupling reaction, a widely used method for forming carbon-carbon bonds. This reaction is essential for the synthesis of a broad range of organic compounds, including those with potential applications in pharmaceuticals and materials science.
Used in the Production of Fluorescent Sensors:
2-Benzylphenylboronic acid is employed in the production of fluorescent sensors for detecting biomolecules such as glucose. These sensors are valuable tools in medical diagnostics and research, enabling the sensitive and selective detection of target molecules.
Used in Cancer and Disease Treatment Research:
2-Benzylphenylboronic acid has been studied for its potential use in the treatment of cancer and other diseases. Its ability to inhibit certain enzymes and disrupt protein-protein interactions makes it a promising candidate for therapeutic applications, particularly in the development of targeted therapies for various diseases.

Upstream product

• 121-43-7 Trimethyl borate 
• 23450-18-2 2-benzyl-1-bromobenzene 
• 71-43-2 benzene 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 40276-68-4 tris(2-benzylphenyl)boroxine 

Downstream Products

• 1341197-47-4 6-phenylphenanthridine-2-carbonitrile 
• 2720-93-6 6-phenylphenanthridine 
• 6327-63-5 C₁₉H₁₂BrN 

Relevant academic research and scientific papers

Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines

An intramolecular oxidative C(sp3)-H amination from unprotected anilines and C(sp3)-H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp3)-H bond (BDE 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process.

Double C-H amination by consecutive SET oxidations

A new method for intramolecular C-H oxidative amination is based on a FeCl3-mediated oxidative reaction of anilines with activated sp3 C-H bonds. The amino group plays multiple roles in the reaction cascade: (1) as the activating group in single-electron-transfer (SET) oxidation process, (2) as a directing group in benzylic/allylic C-H activation at a remote position, and (3) internal nucleophile trapping reactive intermediates formed from the C-H activation steps. These multielectron oxidation reactions proceed with catalytic amounts of Fe(iii) and inexpensive reagents.

Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis

An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.