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Bulk Order 4-Methoxycarbonylphenylboronic acid丨CAS 99768-12-4
4-Methoxycarbonylphenylboronic acid (CAS 99768-12-4), also known as 4-(methoxycarbonyl)phenylboronic acid or 4-boronobenzoic acid methyl ester, is a multifunctional aromatic organoboron compound containing a boronic acid group and a methyl ester substituent at the para-position of a benzene ring. Its two functional groups provide complementary synthetic opportunities: the boronic acid enables carbon–carbon bond formation, while the methyl ester offers a convenient handle for further chemical modification. This compound is a valuable building block for pharmaceutical intermediates, functionalized biaryl compounds, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C8H9BO4/c1-13-8(10)6-2-4-7(5-3-6)9(11)12/h2-5,11-12H,1H3 |
| InChI Key | PQCXFUXRTRESBD-UHFFFAOYSA-N |
| Smiles | O=C(C1=CC=C(B(O)O)C=C1)OC |
| EC No. | 619-459-9 |
| MDL No. | MFCD01632203 |
| PubChem CID | 2734369 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-Methoxycarbonylphenylboronic acid is a useful coupling partner in Suzuki–Miyaura reactions for preparing ester-functionalized 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. The para-positioned methyl ester can remain available for subsequent transformations, enabling the preparation of multifunctional aromatic structures.
Applications in Pharmaceutical Intermediate Synthesis
This compound serves as a building block for preparing ester-containing aromatic intermediates used in pharmaceutical research. Its boronic acid functionality supports the construction of biaryl frameworks, while the methyl ester can be hydrolyzed to a carboxylic acid or converted into other derivatives under suitable conditions. These complementary reaction pathways support multistep synthesis and the preparation of structurally diverse pharmaceutical building blocks.
Applications in Medicinal Chemistry
In medicinal chemistry, 4-Methoxycarbonylphenylboronic acid provides a convenient route for introducing a para-substituted aromatic unit with an ester functionality. The ester group offers opportunities for further derivatization, including conversion into carboxylic acids, amides, and other related structures. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to explore the effects of aromatic substitution.
Applications in Heterocyclic Compound Synthesis
The methyl ester group provides opportunities for additional transformations in the preparation of heterocyclic compounds. Following suitable cross-coupling reactions, the ester functionality may be converted into other reactive groups or incorporated into subsequent cyclization strategies. These approaches are relevant to the synthesis of nitrogen- and oxygen-containing heterocycles for pharmaceutical and specialty chemical research.
