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(4-Methoxyphenyl)boronic acid (CAS 5720-07-0), also known as 4-methoxybenzeneboronic acid or p-anisylboronic acid, is an arylboronic acid containing a methoxy group at the para position of the benzene ring. Its structure combines the reactivity of the boronic acid functionality with the electronic properties of an electron-donating methoxy substituent. This makes it a valuable building block for carbon–carbon bond formation, particularly in Suzuki–Miyaura cross-coupling reactions. It is widely useful in organic synthesis, medicinal chemistry, and the preparation of functional aromatic compounds.
Chemical Identifiers
| InChI | 1S/C7H9BO3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3 |
| InChI Key | VOAAEKKFGLPLLU-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC(=C1)OC)B(O)O |
| EC No. | 611-482-2 |
| MDL No. | MFCD00039139 |
| PubChem CID | 201262 |
Applications
Applications in Pharmaceutical and Agrochemical Intermediate Synthesis
(4-Methoxyphenyl)boronic acid is used to introduce a 4-methoxyphenyl group into pharmaceutical intermediates and other biologically relevant molecular structures. Through palladium-catalyzed Suzuki–Miyaura coupling with suitable aryl or heteroaryl halides, it enables the synthesis of substituted biaryl and heterobiaryl compounds. The methoxyphenyl group is an important structural motif in medicinal chemistry, where it can influence molecular polarity, electronic distribution, lipophilicity, and potential biological activity. Researchers can use this reagent to prepare compound libraries, modify lead structures, and explore structure–activity relationships during drug discovery and development.
Applications in Organic Synthesis and Cross-Coupling Reactions
A major application of (4-Methoxyphenyl)boronic acid is Suzuki–Miyaura cross-coupling. In the presence of an appropriate palladium catalyst and base, its aryl group can be transferred to an organic coupling partner, forming a new carbon–carbon bond. This provides an effective route to 4-methoxy-substituted biphenyls, heterobiaryl compounds, and other functional aromatic structures. The para-methoxy substituent also offers an electronic feature that can be retained for subsequent transformations or used to influence the properties of the resulting products. Its versatility makes it valuable in multi-step synthesis, catalyst screening, and the preparation of specialized aromatic intermediates.
Applications in Organic Electronics and Functional Materials
Methoxy-substituted aromatic compounds are useful in research on conjugated molecules and functional organic materials. The electron-donating methoxy group can influence the electronic characteristics of aromatic structures, making (4-Methoxyphenyl)boronic acid a useful precursor for synthesizing compounds with tailored electronic and optical properties. Through cross-coupling with suitable aromatic partners, researchers can prepare extended conjugated molecules and investigate their potential in organic semiconductors, optoelectronic materials, and functional molecular systems. The reagent is particularly useful when a para-methoxyphenyl unit is required as part of a larger molecular framework.
Applications in Chemical Research and Method Development
In synthetic chemistry laboratories, (4-Methoxyphenyl)boronic acid serves as a practical reagent for developing and optimizing carbon–carbon coupling reactions. Its defined substitution pattern enables the preparation of structurally consistent products for comparative studies. It can be incorporated into research involving palladium catalysis, heterocyclic chemistry, functional group modification, and the synthesis of aromatic reference compounds. Its combination of an arylboronic acid group and a methoxy substituent also makes it a useful substrate for investigating the influence of electronic effects on reaction performance.
