4-methylphenylboronic acid
Semiconductor Display Materials 2025-03-04
4-Methylphenylboronic acid, also known as 4-Tolylboronic acid, is a versatile organoboron compound with a methyl substituent at the 4-position of the phenyl ring and a boronic acid group. This compound is widely used in organic synthesis, material science, and pharmaceutical research due to its unique reactivity and structural properties.
Key Properties
| Property | Details |
|---|---|
| IUPAC Name | 4-Methylphenylboronic acid |
| CAS Number | 5720-05-8 |
| Molecular Formula | C₇H₉BO₂ |
| Molecular Weight | 135.96 g/mol |
| Category | Phenylboronic acid derivative, Pharmaceutical intermediate |
| Appearance | White to light yellow crystalline powder |
| Boiling Point | ~275.2°C |
| Melting Point | 256-263°C |
| Density | ~1.1 g/cm³ |
| Storage Conditions | Sealed, in a cool, dry place |
| Synthesis Method | Various methods including sulfonation and hydroboration |
| Applications | Suzuki coupling reactions, Drug synthesis, Material science |
Synthesis
4-Methylphenylboronic acid can be synthesized through various methods. One approach involves the sulfonation of 4-bromo-2.6-difluorobenzyl alcohol, followed by hydroboration with alkylborohydride lithium and subsequent hydrolysis and recrystallization to yield 4-methylphenylboronic acid. Another method involves the reaction of 4-bromotoluene Grignard reagent with trimethyl borate, followed by hydrolysis and recrystallization to obtain the desired product.
Applications
In organic synthesis, 4-Methylphenylboronic 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 2-cyano-4’-methylbiphenyl, which is a key intermediate in the preparation of sartan-class antihypertensive drugs. Additionally, it serves as an intermediate in the synthesis of liquid crystal materials, highlighting its potential in advanced material applications.
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