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Tolylboronic acid丨CAS 5720-05-8 Bulk Supplier
Tolylboronic acid (CAS 5720-05-8) is an organoboron compound belonging to the arylboronic acid family. It contains a methyl-substituted phenyl ring attached to a boronic acid group, making it a useful building block for carbon–carbon bond formation and the synthesis of substituted aromatic compounds. Its principal application is in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions, where it enables the introduction of a tolyl group into aromatic and heteroaromatic structures. The methyl substituent provides an additional structural feature that can influence molecular properties and reactivity, making this compound valuable in pharmaceutical research, fine chemical synthesis, and functional materials development.
Chemical Identifiers
| InChI | 1S/C7H9BO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5,9-10H,1H3 |
| InChI Key | BIWQNIMLAISTBV-UHFFFAOYSA-N |
| Smiles | C1=C(B(O)O)C=CC(=C1)C |
| EC No. | 611-480-1 |
| MDL No. | MFCD00039138 |
| PubChem CID | 79799 |
Applications
Applications in Pharmaceutical and Agrochemical Intermediate Synthesis
Tolylboronic acid is useful for preparing pharmaceutical intermediates containing methyl-substituted aromatic structures. Through Suzuki–Miyaura coupling with suitable aryl or heteroaryl halides, it facilitates the formation of biaryl and heterobiaryl compounds. Methyl-substituted phenyl groups are common structural elements in medicinal chemistry, where their position can influence molecular shape, hydrophobicity, and interactions with biological targets. Researchers can use this reagent to modify aromatic frameworks, expand compound libraries, and investigate structure–activity relationships during drug discovery and pharmaceutical intermediate development.
Applications in Organic Synthesis and Cross-Coupling Reactions
One of the main applications of Tolylboronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. Under suitable reaction conditions, its tolyl group can be transferred to an organic coupling partner, such as an aryl or heteroaryl halide, to construct a new carbon–carbon bond. This transformation provides access to methyl-substituted biphenyls and other functional aromatic compounds. The methyl group can also serve as a structural feature for subsequent chemical modification or influence the electronic and steric characteristics of the resulting molecules. Its utility in coupling chemistry makes it suitable for multi-step synthesis, reaction optimization, and the preparation of diverse aromatic intermediates.
Applications in Heterocyclic Chemistry
Tolylboronic acid can be coupled with halogenated nitrogen-, oxygen-, or sulfur-containing heterocycles to prepare tolyl-substituted heteroaromatic compounds. These structures are relevant to medicinal chemistry, agrochemical research, and the development of specialty chemicals. By combining a methyl-substituted phenyl group with different heterocyclic frameworks, researchers can adjust molecular properties and explore new structural combinations. This makes the reagent a useful option for synthesizing heterobiaryl compounds and expanding the diversity of functional molecules.
Applications in Organic Electronics and Materials Research
Methyl-substituted aromatic units are used in the development of functional organic molecules and advanced materials. Tolylboronic acid provides a convenient synthetic route for incorporating these units into larger conjugated structures through cross-coupling reactions. The resulting compounds may be investigated as intermediates for organic semiconductors, optoelectronic molecules, and other functional material systems. The methyl substituent can influence molecular geometry, solubility, and packing behavior, depending on the structure of the coupled product. This makes Tolylboronic acid useful in research involving molecular design and structure–property relationships.
