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Bulk Inquiry 4-tert-Butylphenylboronic acid丨CAS 123324-71-0
4-tert-Butylphenylboronic acid (CAS 123324-71-0), also known as 4-(tert-butyl)benzeneboronic acid, is an aromatic organoboron compound containing a boronic acid group and a tert-butyl substituent at the para-position of a benzene ring. The bulky tert-butyl group contributes steric characteristics and hydrophobicity, while the boronic acid functionality enables carbon–carbon bond formation. This compound is a useful building block for pharmaceutical intermediate synthesis, functionalized biaryl compounds, organic materials research, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C10H15BO2/c1-10(2,3)8-4-6-9(7-5-8)11(12)13/h4-7,12-13H,1-3H3 |
| InChI Key | MNJYZNVROSZZQC-UHFFFAOYSA-N |
| Smiles | CC(C1=CC=C(B(O)O)C=C1)(C)C |
| EC No. | 602-928-7 |
| MDL No. | MFCD01009697 |
| PubChem CID | 2734320 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-tert-Butylphenylboronic acid is a useful coupling partner in Suzuki–Miyaura reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under suitable palladium-catalyzed conditions, its boronic acid group reacts with compatible aromatic halides to form new carbon–carbon bonds. This transformation enables the introduction of a para-tert-butylphenyl fragment into complex aromatic structures while retaining the bulky alkyl substituent.
Applications in Pharmaceutical Intermediate Synthesis
This compound serves as a building block for preparing alkyl-substituted aromatic intermediates in pharmaceutical research. Its boronic acid functionality supports the construction of complex molecular frameworks, while the tert-butyl group can influence molecular lipophilicity, steric properties, and interactions with biological targets. These characteristics make it relevant to the preparation of specialized pharmaceutical intermediates and structurally diverse research compounds.
Applications in Medicinal Chemistry
In medicinal chemistry, 4-tert-Butylphenylboronic acid provides a convenient route for incorporating a bulky hydrophobic aromatic fragment into candidate molecules. The tert-butyl substituent can influence molecular conformation, binding interactions, and physicochemical properties. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to investigate the effects of steric and hydrophobic substitution.
Applications in Functionalized Biaryl Synthesis
The compound is valuable for constructing biaryl structures containing a defined para-tert-butylphenyl fragment. Its boronic acid group enables coupling with selected aromatic partners, while the tert-butyl substituent can influence solubility, molecular packing, and intermolecular interactions. These properties support the preparation of advanced aromatic intermediates and the investigation of molecular structure–property relationships.
