4-Pentylphenylboronic acid
Semiconductor Display Materials 2025-03-04
4-Pentylphenylboronic acid, also known as p-Pentylphenylboronic acid, is an organoboron compound with a pentyl substituent at the 4-position of the phenyl ring and a boronic acid group. This compound is a valuable building block in organic synthesis, material science, and pharmaceutical research due to its unique reactivity and structural properties.
Key Properties
| Property | Details |
|---|---|
| IUPAC Name | 4-Pentylphenylboronic acid |
| CAS Number | 121219-12-3 |
| Molecular Formula | C₁₁H₁₇BO₂ |
| Molecular Weight | 192.06 g/mol |
| Category | Phenylboronic acid derivative, Pharmaceutical intermediate |
| Appearance | Tan powder |
| Boiling Point | ~328°C |
| Melting Point | 82-84°C |
| Density | ~1.01 g/cm³ |
| Storage Conditions | Sealed, in a cool, dry place |
| Synthesis Method | Organic lithium reagent method, Grignard reagent method |
| Applications | Suzuki coupling reactions, Drug synthesis, Material science |
Synthesis
4-Pentylphenylboronic acid can be synthesized using various methods, primarily involving organic lithium reagents or Grignard reagents. One specific approach involves using 4-bromophenylacetone as the starting material, which undergoes carbonyl protection, Grignard reaction, and dihydroxyboron substitution to yield 4-pentylphenylboronic acid.
Applications
In organic synthesis, 4-Pentylphenylboronic acid is a crucial intermediate for preparing complex molecules, especially those requiring defined stereochemistry and functionality. It is widely used in Suzuki coupling reactions, which are essential for forming carbon-carbon bonds in organic synthesis.
The compound is also used in the synthesis of various drug intermediates, highlighting its importance in pharmaceutical research. Additionally, it serves as an intermediate in the synthesis of liquid crystal materials, showcasing its potential in advanced material applications.
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