4-Vinylphenylboronic Acid (CAS 2156-04-9) is a fascinating molecule that bridges the gap between fundamental organic chemistry and applied industrial processes. Its dual nature, boasting both a boronic acid group essential for cross-coupling reactions and a vinyl group capable of polymerization, makes it a compound of significant interest to synthetic chemists, material scientists, and pharmaceutical developers.

Understanding the Structure and Properties

At its core, 4-Vinylphenylboronic Acid is a benzene ring substituted with a vinyl group (-CH=CH₂) and a boronic acid group (-B(OH)₂). This arrangement allows it to participate in a variety of chemical transformations. Typically appearing as a white to light beige crystalline powder, it exhibits moderate solubility in common organic solvents like ethanol and THF, but limited solubility in water. Its melting point, generally between 190-193 °C, indicates a stable solid form under standard laboratory conditions.

Synthesis of 4-Vinylphenylboronic Acid

The synthesis of 4-Vinylphenylboronic Acid often involves established organometallic chemistry. A common route involves the preparation of a Grignard reagent from 4-chlorostyrene, followed by reaction with trimethyl borate. Subsequent acidic hydrolysis yields the target boronic acid. Achieving high yields and purity in this synthesis requires careful control of anhydrous conditions and reaction temperatures, a testament to the precision required in fine chemical manufacturing.

Key Chemical Applications:

  • Suzuki-Miyaura Coupling: This is perhaps the most prominent application. The boronic acid group readily undergoes transmetalation with palladium catalysts, enabling the formation of C-C bonds with aryl or vinyl halides. This makes it invaluable in synthesizing complex pharmaceuticals, agrochemicals, and advanced organic materials.
  • Polymerization: The vinyl group can undergo radical or other types of polymerization, allowing 4-Vinylphenylboronic Acid to be incorporated into polymer backbones. This creates polymers with pendant boronic acid functionalities, useful for sensors, drug delivery, or self-healing materials.
  • Ligand Synthesis: Boronic acids can sometimes be used as precursors for specialized ligands in catalysis.

Sourcing Quality 4-Vinylphenylboronic Acid

For researchers and manufacturers looking to buy 4-Vinylphenylboronic Acid, partnering with experienced chemical suppliers is crucial. A reputable manufacturer will provide detailed specifications, including its CAS number (2156-04-9), and ensure consistent quality. Understanding the price and availability from different sources, particularly established chemical hubs like China, can optimize your procurement strategy.

By appreciating the chemical synthesis and diverse applications of 4-Vinylphenylboronic Acid, chemists can effectively leverage this powerful intermediate in their ongoing innovation and production efforts.