• 1. An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Fluorobenzenes
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

2-Bromo-5-Methyl-6-Fluorophenylboronic Acid (CAS No. 957061-15-3): A Comprehensive Overview

The compound 2-bromo-5-methyl-6-fluorophenylboronic acid (CAS No. 957061-15-3) is a highly specialized aromatic boronic acid derivative with significant applications in organic synthesis, particularly in the field of medicinal chemistry and materials science. This compound is characterized by its unique substitution pattern, featuring a bromine atom at the 2-position, a methyl group at the 5-position, and a fluorine atom at the 6-position on the phenyl ring. The presence of these substituents imparts distinct electronic and steric properties, making it a valuable building block for constructing complex molecular architectures.

Boronic acids, such as 2-bromo-5-methyl-6-fluorophenylboronic acid, are widely recognized for their reactivity in cross-coupling reactions, most notably the Suzuki-Miyaura coupling. This reaction facilitates the formation of carbon-carbon bonds between boronic acids and aryl or alkenyl halides in the presence of palladium catalysts. The versatility of this compound lies in its ability to participate in various coupling reactions, enabling the synthesis of biaryl compounds, which are critical intermediates in drug discovery and material synthesis.

Recent advancements in organoboron chemistry have further highlighted the importance of 2-bromo-5-methyl-6-fluorophenylboronic acid in constructing functional materials. For instance, researchers have employed this compound to synthesize novel π-conjugated systems with enhanced electronic properties, paving the way for applications in organic electronics and optoelectronics. The methyl and fluorine substituents on the phenyl ring not only influence the electronic characteristics but also play a crucial role in modulating the molecule's solubility and stability during synthetic processes.

In terms of synthesis, 2-bromo-5-methyl-6-fluorophenylboronic acid can be prepared via several routes, including nucleophilic aromatic substitution and metal-mediated coupling reactions. One common method involves the bromination of a methyl-substituted phenylboronic acid followed by fluorination at specific positions. The regioselectivity of these reactions is often controlled by directing groups, ensuring that the substituents occupy their desired positions on the aromatic ring.

The applications of 2-bromo-5-methyl-6-fluorophenylboronic acid extend beyond traditional organic synthesis. In medicinal chemistry, this compound serves as a key intermediate in the development of bioactive molecules targeting various therapeutic areas, such as cancer and inflammation. Its ability to undergo multiple transformations makes it an ideal candidate for constructing multi-functional drug candidates with tailored pharmacokinetic profiles.

From an environmental perspective, researchers have also explored the use of 2-bromo-5-methyl-6-fluorophenylboronic acid in green chemistry initiatives. By incorporating this compound into catalytic cycles or recyclable systems, scientists aim to reduce waste and improve sustainability in chemical manufacturing processes.

In conclusion, 2-bromo-5-methyl-6-fluorophenylboronic acid (CAS No. 957061-15-3) stands as a testament to the ingenuity of modern organic chemistry. Its unique structure, reactivity, and versatility continue to drive innovation across diverse fields, making it an indispensable tool for researchers and industry professionals alike.

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• 139911-27-6((4-fluoro-3-methylphenyl)boronic acid)
• 168267-99-0(3-Fluoro-4-methylphenylboronic acid)
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• 144025-03-6((2,4-difluorophenyl)boronic acid)
• 1993-03-9(2-Fluorophenylboronic acid)