4-trans-ethylcyclohexylphenylboronic acid
Semiconductor Display Materials 2025-03-04
4-trans-Ethylcyclohexylphenylboronic acid is an organoboron compound featuring an ethylcyclohexyl substituent on the phenyl ring and a boronic acid group. This compound is of interest in organic synthesis and material science due to its unique structure and versatile reactivity.
Key Properties
| Property | Details |
|---|---|
| IUPAC Name | 4-trans-Ethylcyclohexylphenylboronic acid |
| CAS Number | 164220-57-9 |
| Molecular Formula | C₁₄H₂₁BO₂ |
| Molecular Weight | 232.13 g/mol |
| Appearance | White crystalline solid |
| Density | 1.05 g/cm³ (predicted) |
| Boiling Point | ~381.8°C (predicted) |
| Acidity (pKa) | 8.70±0.17 (predicted) |
| Synthesis Method | Palladium-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura coupling) |
| Applications | Organic synthesis, medicinal chemistry, development of novel pharmaceuticals |
Synthesis
4-trans-Ethylcyclohexylphenylboronic acid can be synthesized via palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling. This method involves the reaction of a brominated phenylboronic acid with a bromoethylcyclohexane, facilitated by a palladium catalyst, to construct the ethylcyclohexylphenylboronic acid efficiently.
Applications
In organic synthesis, 4-trans-Ethylcyclohexylphenylboronic acid serves as a valuable building block for the preparation of complex molecules, particularly those requiring defined stereochemistry and functionality. The ethylcyclohexylphenyl structure makes it a promising candidate for the development of novel pharmaceuticals, agrochemicals, and functional materials. The boronic acid moiety can be further transformed into other functional groups, expanding the scope of its applications.
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