3,4,5-trifluorophenylboronic acid
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Category：Semiconductor Display Materials Own Brand：MT /MOQ:100KG /From China/ B2B only.
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.
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