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Professional Supplier 2-Methoxyphenylboronic acid丨CAS 5720-06-9
2-Methoxyphenylboronic acid (CAS 5720-06-9), also known as 2-methoxybenzeneboronic acid or o-anisylboronic acid, is an organoboron compound featuring a boronic acid group and a methoxy substituent at the ortho position of a benzene ring. Its structure makes it a useful reagent for introducing the 2-methoxyphenyl group into more complex organic molecules. As an arylboronic acid, it is particularly valuable in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions, supporting the synthesis of biaryl and heterobiaryl compounds for pharmaceutical research, organic synthesis, and functional materials development.
Chemical Identifiers
| InChI | 1S/C7H9BO3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5,9-10H,1H3 |
| InChI Key |
ROEQGIFOWRQYHD-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=CC=C1OC)O |
| EC No. | 611-481-7 |
| MDL No. | MFCD00236047 |
| PubChem CID | 2733958 |
Applications
Applications in Pharmaceutical and Agrochemical Intermediate Synthesis
2-Methoxyphenylboronic acid is used to prepare pharmaceutical intermediates containing the 2-methoxyphenyl structural motif. Through Suzuki–Miyaura coupling with suitable aryl or heteroaryl halides, it enables the formation of carbon–carbon bonds and provides access to diverse substituted aromatic structures. Ortho-methoxy-substituted biaryl frameworks are of interest in medicinal chemistry because the position of the methoxy group can influence molecular conformation, steric interactions, polarity, and biological activity. Researchers can use this reagent to modify lead compounds, prepare compound libraries, and investigate structure–activity relationships during drug discovery and development.
Applications in Organic Synthesis and Cross-Coupling Reactions
A principal application of 2-Methoxyphenylboronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. In the presence of an appropriate catalyst and base, the 2-methoxyphenyl group can be transferred to an organic coupling partner, such as an aryl or heteroaryl halide. This reaction provides an effective route to ortho-methoxy-substituted biphenyls and other functional aromatic compounds. The ortho position of the methoxy group introduces steric and electronic effects that can influence the conformation and reactivity of the resulting molecules. These characteristics make the compound useful in multi-step synthetic routes and the preparation of structurally diverse intermediates.
Applications in Heterocyclic Chemistry and Functional Molecules
The combination of an aromatic ring and an electron-donating methoxy group makes 2-Methoxyphenylboronic acid useful in the synthesis of heteroaromatic and other functional molecules. Coupling with halogenated nitrogen-, oxygen-, or sulfur-containing heterocycles can provide access to methoxyphenyl-substituted heterocycles. Such structures are frequently explored in medicinal chemistry and advanced organic synthesis. The reagent therefore offers a practical way to expand molecular diversity and introduce specific aromatic substitution patterns into target compounds.
Applications in Organic Electronics and Materials Research
Methoxy-substituted aromatic units can influence the electronic and optical properties of conjugated molecular systems. 2-Methoxyphenylboronic acid can be used to construct extended aromatic structures through cross-coupling with suitable partners. The resulting compounds may serve as intermediates in research on organic semiconductors, optoelectronic molecules, and other functional materials. Its ortho substitution pattern also allows researchers to investigate how steric effects and molecular geometry influence conjugation, packing behavior, and material properties.
