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Best Supplier 2-(Methoxycarbonyl)benzeneboronic acid丨CAS 374538-03-1
2-(Methoxycarbonyl)benzeneboronic acid (CAS 374538-03-1), also known as 2-(methoxycarbonyl)phenylboronic acid or 2-boronobenzoic acid methyl ester, is a multifunctional aromatic organoboron compound featuring a boronic acid group and a methyl ester group at adjacent positions on a benzene ring. The compound combines the synthetic versatility of an arylboronic acid with the chemical reactivity of a carboxylic acid ester, providing two distinct functional groups for further molecular modification. The ortho-substitution pattern is particularly useful for constructing complex aromatic structures and developing synthetic routes involving neighboring functional groups. These characteristics make 2-(Methoxycarbonyl)benzeneboronic acid a valuable building block for medicinal chemistry, pharmaceutical intermediate synthesis, Suzuki–Miyaura cross-coupling reactions, heterocyclic chemistry, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C8H9BO4/c1-13-8(10)6-4-2-3-5-7(6)9(11)12/h2-5,11-12H,1H3 |
| InChI Key | ODAXNYMENLFYMY-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=CC=C1C(OC)=O)O |
| EC No. | 640-205-8 |
| MDL No. | MFCD02179452 |
| PubChem CID | 2773496 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-(Methoxycarbonyl)benzeneboronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted aromatic compounds and functionalized biaryl derivatives. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation enables the introduction of an ortho-methoxycarbonyl-substituted phenyl fragment into more complex molecular frameworks. The methyl ester functionality may remain available for subsequent transformations, depending on the reaction conditions. Because the boronic acid and ester groups occupy adjacent positions, steric effects and possible intramolecular interactions should be considered when optimizing coupling reactions.
Applications in Medicinal Chemistry
In medicinal chemistry, 2-(Methoxycarbonyl)benzeneboronic acid serves as a useful building block for preparing aromatic research compounds and investigating structure–activity relationships. The boronic acid functionality enables the introduction of a substituted phenyl group into candidate molecules, while the methyl ester provides an additional site for chemical modification. The ester group can be transformed into other functional groups through suitable reactions, allowing researchers to prepare structurally diverse analogs. These characteristics make the compound relevant to lead optimization, molecular library synthesis, and the development of aromatic intermediates containing carboxyl-derived functionality.
Applications in Pharmaceutical Intermediate Synthesis
2-(Methoxycarbonyl)benzeneboronic acid may support pharmaceutical research programs requiring intermediates containing an ortho-substituted aromatic framework. Through suitable cross-coupling reactions, the compound can be incorporated into biaryl or aryl–heteroaryl structures while retaining the methyl ester group when compatible conditions are used. The ester functionality may subsequently undergo hydrolysis, amidation through appropriate intermediates, or other selected transformations to produce compounds with different chemical properties. This combination of functional groups provides flexibility for multistep synthesis and enables the preparation of advanced pharmaceutical research intermediates.
Applications in Cyclopropyl-Substituted Heterocyclic Synthesis
The adjacent boronic acid and methyl ester groups make 2-(Methoxycarbonyl)benzeneboronic acid useful for preparing intermediates that may undergo further transformations into heterocyclic compounds. After suitable carbon–carbon bond formation, the ester group can be converted into a carboxylic acid, amide, alcohol, or other functional group as required by the synthetic route. In appropriately designed molecular systems, these transformations may support subsequent intramolecular cyclization reactions. Researchers may use this compound to develop routes toward fused aromatic and heterocyclic structures, although the feasibility of each cyclization depends on the functional groups and reaction conditions involved.
