(3-Fluoro-4 ‘- propyl – [1,1’ – biphenyl] -4-yl) boronic acid

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Introduction

(3-Fluoro-4′-propyl-[1.1′-biphenyl]-4-yl)boronic acid is a fluorinated biphenyl boronic acid derivative with potential applications in organic synthesis and medicinal chemistry. This compound is characterized by its unique molecular structure, combining a fluorine atom at the meta position of one benzene ring and a propyl substituent on the adjacent ring. The boronic acid group is located at the para position relative to the propyl group, providing a reactive site for various coupling reactions.

Key Properties

The compound exhibits good stability under normal conditions and can be stored at room temperature. It is soluble in common organic solvents, facilitating its use in various reaction media. The presence of the fluorine atom imparts unique electronic and steric properties to the molecule, influencing its reactivity and biological activity.

Synthesis

The synthesis of (3-Fluoro-4′-propyl-[1.1′-biphenyl]-4-yl)boronic acid typically involves palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling. This method allows for the efficient construction of the biphenyl framework by coupling a fluorinated aryl halide with a propyl-substituted arylboronic acid.

Applications

In organic synthesis, this compound serves as a valuable building block for the preparation of complex molecules with defined stereochemistry and functionality. Its fluorinated biphenyl structure makes it a promising candidate for the development of novel pharmaceuticals, agrochemicals, and functional materials. The boronic acid moiety can be further transformed into other functional groups, expanding the scope of its applications.

Property Details
IUPAC Name (3-Fluoro-4′-propyl-[1.1′-biphenyl]-4-yl)boronic acid
CAS Number 909709-42-8
Molecular Formula C₁₅H₁₆BFO₂
Molecular Weight 258.0992 g/mol
Appearance White to off-white powder
Density 1.17±0.1 g/cm³ (Predicted)
Boiling Point 412.5±55.0 °C (Predicted)
Refractive Index 1.567
Flash Point 203.3±31.5 °C
Synthesis Method Palladium-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura coupling)
Applications Organic synthesis, medicinal chemistry, development of novel pharmaceuticals

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