3,4,5-trifluorophenylboronic acid

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Introduction

3.4.5-Trifluorophenylboronic acid is a valuable organoboron compound with three fluorine substituents on the phenyl ring and a boronic acid group. This compound finds extensive applications in organic synthesis and material science, leveraging its unique reactivity and structural properties.

Key Properties

Property Details
IUPAC Name 3.4.5-Trifluorophenylboronic acid
CAS Number 143418-49-9
Molecular Formula C₆H₄BF₃O₂
Molecular Weight 175.90 g/mol
Category Phenylboronic acid derivative, Pharmaceutical intermediate
Appearance Tan solid powder
Boiling Point ~263.6°C
Melting Point 290-295°C
Density ~1.447 g/cm³
Refractive Index 1.423-1.425
Storage Conditions Cool, dark place, sealed
Synthesis Method Reaction of 3.4.5-trifluorobromobenzene with trimethoxyborane
Applications Suzuki coupling reactions, Chan-Lam coupling reactions, Pharmaceutical intermediates

Synthesis

3.4.5-Trifluorophenylboronic acid can be synthesized through the reaction of 3.4.5-trifluorobromobenzene with trimethoxyborane. The process involves reacting 3.4.5-trifluorobromobenzene with trimethoxyborane in the presence of a suitable catalyst and solvent. After purification, 3.4.5-Trifluorophenylboronic acid is obtained.

Alternatively, 3.4.5-trifluorobromobenzene can be prepared from o-dichlorobenzene via a multi-step process involving sulfonation, nitration, esterification, chloro-fluorination, hydrolysis, bromination, reduction, and diazotization-fluorination. This method offers a route with fewer by-products and simpler post-treatment.

Applications

In organic synthesis, 3.4.5-Trifluorophenylboronic acid is a crucial building block for preparing complex molecules, especially those requiring defined stereochemistry and functionality. It is widely used in Suzuki coupling reactions, which are vital for forming carbon-carbon bonds in organic synthesis. Additionally, the compound undergoes Chan-Lam coupling reactions in the presence of transition metal copper, yielding ether and amine derivatives.

The boronic acid group can be further transformed into other functional groups, expanding the scope of its applications. As a pharmaceutical intermediate, 3.4.5-Trifluorophenylboronic acid has broad application prospects.

Disclaimer: The above content is for reference and communication only among industry insiders, and does not guarantee its accuracy or completeness. According to relevant laws and regulations and the regulations of this website, units or individuals who purchase related items should obtain valid qualifications and qualification conditions.

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