4-trifluoromethoxyphenylboronic acid
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Category：Semiconductor Display Materials MOQ:100KG Shipped directly from China
Introduction
4-Trifluoromethoxyphenylboronic acid is a valuable organoboron compound with a trifluoromethoxy substituent at the 4-position of the phenyl ring and a boronic acid group. This compound finds extensive applications in organic synthesis, material science, and pharmaceutical research due to its unique reactivity and structural properties.
Key Properties
| Property | Details |
|---|---|
| IUPAC Name | 4-Trifluoromethoxyphenylboronic acid |
| CAS Number | 139301-27-2 |
| Molecular Formula | C₇H₆BF₃O₃ |
| Molecular Weight | 205.93 g/mol |
| Category | Phenylboronic acid derivative, Pharmaceutical intermediate |
| Appearance | White to beige crystalline powder |
| Boiling Point | ~256.6°C |
| Melting Point | 123-127°C |
| Density | ~1.4 g/cm³ |
| Storage Conditions | Sealed, in a cool, dry place |
| Synthesis Method | Reaction of 1-bromo-4-(trifluoromethoxy)benzene with boron triisopropoxide |
| Applications | Suzuki coupling reactions, Drug synthesis, Material science |
Synthesis
4-Trifluoromethoxyphenylboronic acid can be synthesized through the reaction of 1-bromo-4-(trifluoromethoxy)benzene with boron triisopropoxide in the presence of 2.25 M butyllithium in hexane. The reaction mixture is stirred, acidified, and then separated and dried to obtain the desired product.
Applications
In organic synthesis, 4-Trifluoromethoxyphenylboronic 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.
The compound is also used in the synthesis of biologically active molecules, such as lactate dehydrogenase inhibitors for use against cancer cell proliferation, nitro-phenoxybenzoic acid derivatives for PAI-1 inhibition, and PA-824 analogs for use as antituberculosis drugs. Additionally, it serves as a modulator of survival motor neuron protein.
In material science, 4-Trifluoromethoxyphenylboronic acid is used as an intermediate in the synthesis of liquid crystal materials, highlighting its potential in advanced material applications.
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