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Scientific Supply 3-Acetylphenylboronic acid丨CAS 204841-19-0
3-Acetylphenylboronic acid (CAS 204841-19-0), also known as 3-acetylbenzeneboronic acid or (3-acetylphenyl)boronic acid, is a multifunctional aromatic organoboron compound containing a boronic acid group and an acetyl group at the meta-positions of a benzene ring. Its structure combines the synthetic versatility of an arylboronic acid with the chemical reactivity of an aromatic ketone. The boronic acid functionality enables carbon–carbon bond formation, while the acetyl group provides an additional site for chemical modification. These characteristics make the compound a useful building block for medicinal chemistry, pharmaceutical intermediate development, heterocyclic synthesis, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C8H9BO3/c1-6(10)7-3-2-4-8(5-7)9(11)12/h2-5,11-12H,1H3 |
| InChI Key | SJGGDZCTGBKBCK-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC=C1C(=O)C)B(O)O |
| EC No. | 629-232-6 |
| MDL No. | MFCD01074678 |
| PubChem CID | 2734310 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3-Acetylphenylboronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides to form new carbon–carbon bonds. This transformation enables the introduction of a meta-acetylphenyl fragment into more complex molecular frameworks. The acetyl group may remain intact under suitable coupling conditions, allowing further modification of the resulting intermediates.
Applications in Medicinal Chemistry
In medicinal chemistry, 3-Acetylphenylboronic acid serves as a building block for preparing aromatic compounds containing ketone functionality. The acetyl group can influence molecular polarity and provide opportunities for additional structural modification. Researchers may use this compound to introduce an acetyl-substituted phenyl fragment into pharmaceutical research molecules through suitable coupling reactions. The resulting derivatives can be investigated in lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
3-Acetylphenylboronic acid may support pharmaceutical intermediate synthesis requiring aromatic structures with a reactive carbonyl group. The boronic acid functionality enables the construction of substituted aromatic frameworks, while the acetyl group can undergo selected transformations such as reduction, condensation, and oxime formation. These reactions provide opportunities to introduce additional functional groups or construct more complex molecular structures. This dual functionality makes the compound useful for developing flexible multistep synthetic routes.
Applications in Heterocyclic Compound Synthesis
The acetyl functionality makes 3-Acetylphenylboronic acid relevant to heterocyclic synthesis. Aromatic methyl ketones can participate in selected condensation and cyclization reactions used to construct nitrogen-, oxygen-, and sulfur-containing heterocycles. After suitable cross-coupling reactions, the acetyl-substituted aromatic intermediate may be converted into more complex heterocyclic structures. Researchers may use this approach to prepare substituted pyrazoles, isoxazoles, and other heterocyclic derivatives under appropriate reaction conditions.
