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(3-Methoxyphenyl)boronic acid丨CAS 10365-98-7 Manufacturer
(3-Methoxyphenyl)boronic acid, CAS 10365-98-7, also known as 3-methoxybenzeneboronic acid or 3-anisylboronic acid, is an aromatic organoboron compound featuring a boronic acid group and a methoxy substituent at the meta position of a benzene ring. Its structure combines the versatility of boronic acid chemistry with the electronic characteristics of an electron-donating methoxy group. The boronic acid functionality makes it a valuable building block for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions, enabling the formation of carbon–carbon bonds and the synthesis of diverse biaryl compounds. Its functionalized aromatic structure is widely relevant to pharmaceutical intermediate synthesis, specialty chemical development, and advanced organic research.
Chemical Identifiers
| InChI | 1S/C7H9BO3/c1-11-7-4-2-3-6(5-7)8(9)10/h2-5,9-10H,1H3 |
| InChI Key | NLLGFYPSWCMUIV-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC=C1OC)B(O)O |
| EC No. | 600-467-6 |
| MDL No. | MFCD00161359 |
| PubChem CID | 2734370 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
(3-Methoxyphenyl)boronic acid is useful in medicinal chemistry for introducing a 3-methoxyphenyl group into complex molecular structures. Through Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, it enables the preparation of substituted biaryl and heteroaryl compounds. Methoxy-substituted aromatic groups are frequently incorporated into pharmaceutical research compounds because they can influence molecular polarity, lipophilicity, and electronic properties. The methoxy group can also be converted into a hydroxyl group through appropriate demethylation chemistry, providing additional opportunities for molecular modification. These features make the compound a useful intermediate for drug discovery and pharmaceutical synthesis.
Applications in Biaryl and Heteroaryl Synthesis
The boronic acid group in (3-Methoxyphenyl)boronic acid provides a convenient reaction site for carbon–carbon bond formation with compatible organic electrophiles. Suzuki–Miyaura coupling allows chemists to introduce the 3-methoxyphenyl unit into aromatic and heteroaromatic frameworks, producing a variety of substituted biaryl compounds. The meta-methoxy substitution pattern provides a defined structural arrangement and can influence the electronic characteristics of the resulting molecules. These properties are useful in the preparation of molecular libraries, aromatic intermediates, and compounds designed for further functionalization.
Applications in Natural Product and Bioactive Compound Synthesis
Methoxy-substituted aromatic rings are common structural features in natural product-inspired compounds and bioactive molecule research. (3-Methoxyphenyl)boronic acid can contribute to the construction of these structures by providing a pre-functionalized aromatic building block for cross-coupling reactions. Its use enables the introduction of a methoxy-bearing phenyl group into larger molecular frameworks, supporting the synthesis of natural product analogues and structurally diversified compounds. The possibility of converting the methoxy group into other functionalities further expands its value in multi-step synthesis.
Applications in Specialty Chemicals and Functional Molecules
(3-Methoxyphenyl)boronic acid is also relevant to the preparation of specialty aromatic compounds and functional organic molecules. Through cross-coupling reactions, the methoxyphenyl unit can be incorporated into larger conjugated or aromatic structures for further investigation. The electron-donating methoxy group can influence the electronic distribution of the resulting compounds, making them useful in research involving molecular design and structure–property relationships. Its derivatives may be explored in specialty chemicals, functional organic materials, and advanced molecular synthesis.
