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Bulk Order 3-(Methoxycarbonyl)benzeneboronic acid丨CAS 99769-19-4
3-(Methoxycarbonyl)benzeneboronic acid (CAS 99769-19-4), also known as 3-(methoxycarbonyl)phenylboronic acid or 3-boronobenzoic acid methyl ester, is a multifunctional aromatic organoboron compound containing a boronic acid group and a methyl ester substituent at the meta-position of a benzene ring. Its two distinct functional groups provide complementary synthetic opportunities: the boronic acid supports carbon–carbon bond formation, while the ester can undergo hydrolysis or other transformations. This compound is a valuable building block for pharmaceutical intermediates, functionalized aromatic compounds, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C8H9BO4/c1-13-8(10)6-3-2-4-7(5-6)9(11)12/h2-5,11-12H,1H3 |
| InChI Key | ALTLCJHSJMGSLT-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC=C1C(OC)=O)B(O)O |
| EC No. | 671-671-0 |
| MDL No. | MFCD02093046 |
| PubChem CID | 2734714 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3-(Methoxycarbonyl)benzeneboronic 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 methyl ester can provide an additional functional handle for subsequent transformations, allowing the preparation of more complex 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 enables the construction of biaryl frameworks, while the methyl ester can be hydrolyzed to a carboxylic acid or retained for further synthetic modification. This combination supports multistep synthesis and the preparation of structurally diverse pharmaceutical building blocks.
Applications in Medicinal Chemistry
In medicinal chemistry, 3-(Methoxycarbonyl)benzeneboronic acid provides a convenient route for introducing a meta-substituted aromatic unit containing an ester functionality. The ester group offers opportunities for further derivatization, including conversion into carboxylic acids, amides, and other related structures. Researchers can use this compound in analog synthesis, lead optimization, and structure–activity relationship studies.
Applications in Heterocyclic Compound Synthesis
The methyl ester functionality provides opportunities for intramolecular and multistep transformations that can contribute to the preparation of heterocyclic structures. After suitable cross-coupling reactions, the ester group may be converted into other functional groups or incorporated into subsequent cyclization strategies. These approaches are relevant to the synthesis of nitrogen- and oxygen-containing heterocycles in pharmaceutical and specialty chemical research.
