4-trifluoromethylphenylboronic acid
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Category：Semiconductor Display Materials MOQ:100KG Shipped directly from China
Introduction
4-Trifluoromethylphenylboronic acid is a valuable organoboron compound with a trifluoromethyl substituent at the 4-position of the phenyl ring and a boronic acid group. This compound finds extensive applications in organic synthesis and material science due to its unique reactivity and structural properties.
Key Properties
| Property | Details |
|---|---|
| IUPAC Name | 4-Trifluoromethylphenylboronic acid |
| CAS Number | 128796-39-4 |
| Molecular Formula | C₇H₆BF₃O₂ |
| Molecular Weight | 189.93 g/mol |
| Category | Phenylboronic acid derivative, Pharmaceutical intermediate |
| Appearance | White powder |
| Boiling Point | ~258.6°C |
| Melting Point | 245-250°C |
| Density | ~1.4 g/cm³ |
| Refractive Index | 1.462 |
| Storage Conditions | Sealed, in a cool, dry place |
| Synthesis Method | Reaction of 4-bromomethylbenzoic acid methyl ester with pinacolborane |
| Applications | Suzuki coupling reactions, Chan-Lam coupling reactions, Pharmaceutical intermediates |
Synthesis
4-Trifluoromethylphenylboronic acid can be synthesized through the reaction of 4-bromomethylbenzoic acid methyl ester with pinacolborane, potassium acetate, and [1.1’-bis(diphenylphosphino)ferrocene]dichloropalladium. The process involves reacting these components in a suitable solvent under nitrogen atmosphere. After purification, 4-Trifluoromethylphenylboronic acid is obtained.
Alternatively, 4-trifluoromethylbromobenzene 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, 4-Trifluoromethylphenylboronic 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, 4-Trifluoromethylphenylboronic acid has broad application prospects.
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