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Quality Product 2,3-Dimethoxybenzeneboronic acid丨CAS 40972-86-9
2,3-Dimethoxybenzeneboronic acid, CAS 40972-86-9, is a functionalized aromatic boronic acid featuring two methoxy groups at the 2- and 3-positions of a benzene ring. Its molecular structure combines the reactivity of the boronic acid group with the electronic and steric characteristics of two adjacent methoxy substituents. This makes it a useful building block in organic synthesis, particularly for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions. It provides a route to introduce a dimethoxy-substituted aromatic unit into more complex molecular frameworks and is relevant to pharmaceutical intermediate synthesis, heteroaromatic chemistry, and specialty organic compound development.
Chemical Identifiers
| InChI | 1S/C8H11BO4/c1-12-7-5-3-4-6(9(10)11)8(7)13-2/h3-5,10-11H,1-2H3 |
| InChI Key | VREWSCMOGIXMDQ-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=CC(OC)=C1OC)O |
| EC No. | 670-283-9 |
| MDL No. | MFCD02683112 |
| PubChem CID | 5156491 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
2,3-Dimethoxybenzeneboronic acid is a valuable building block for medicinal chemistry and pharmaceutical research. Its boronic acid group can react with suitable aryl or heteroaryl halides in Suzuki–Miyaura cross-coupling reactions, enabling the formation of carbon–carbon bonds and the preparation of substituted biaryl structures. Dimethoxy-substituted aromatic rings are frequently used in the design of biologically relevant molecules and pharmaceutical intermediates. The two methoxy groups also provide opportunities for subsequent chemical transformations, including demethylation when hydroxyl-functionalized derivatives are required.
Applications in Biaryl and Heteroaryl Synthesis
The compound is suitable for preparing structurally diverse biaryl and heteroaryl compounds. Through cross-coupling with compatible aromatic or heteroaromatic electrophiles, it enables the introduction of a 2,3-dimethoxyphenyl group into target structures. The resulting compounds can serve as intermediates for further functionalization, including modification of the aromatic substituents or extension of the molecular framework. This makes the compound useful in synthetic route development and the preparation of molecular libraries for research applications.
Applications in Natural Product and Bioactive Compound Synthesis
Dimethoxy-substituted aromatic rings occur in a variety of natural product-inspired structures and bioactive compound research. 2,3-Dimethoxybenzeneboronic acid can contribute to the construction of these frameworks by providing a pre-functionalized aromatic building block for carbon–carbon bond formation. Its use in cross-coupling chemistry can help researchers assemble complex aromatic structures and investigate structural variations during the synthesis of natural product analogues and related compounds.
Applications in Specialty Chemicals and Functional Molecules
The two methoxy substituents influence the electronic properties and reactivity of the aromatic ring, making this compound useful in the synthesis of customized functional molecules. The boronic acid group enables the introduction of the dimethoxyphenyl unit into larger molecular structures, while the methoxy groups can be retained or modified according to the target compound. These characteristics support the development of specialty aromatic intermediates and compounds intended for further chemical derivatization.
