Hangzhou Leap Chem Co., Ltd. is one of the most professional manufacturers and suppliers of 3,5-dimethylphenylboronic acid丨cas 172975-69-8 in China. Welcome to wholesale bulk high quality chemical products at competitive price from our factory. If you have any enquiry about custom service, please feel free to email us.
Bulk Supply 3,5-Dimethylphenylboronic acid丨CAS 172975-69-8
3,5-Dimethylphenylboronic acid (CAS 172975-69-8), also known as 3,5-dimethylbenzeneboronic acid, is an aromatic organoboron compound featuring a boronic acid group and two methyl substituents at the 3- and 5-positions of a benzene ring. Its symmetrical substitution pattern provides a defined aromatic building block with electron-donating alkyl groups. The boronic acid functionality enables carbon–carbon bond formation through suitable cross-coupling reactions, while the methyl substituents influence the electronic characteristics, hydrophobicity, and steric environment of the aromatic ring. These properties make the compound useful in medicinal chemistry, pharmaceutical intermediate synthesis, specialty aromatic chemistry, and functional materials research.
Chemical Identifiers
| InChI | 1S/C8H11BO2/c1-6-3-7(2)5-8(4-6)9(10)11/h3-5,10-11H,1-2H3 |
| InChI Key | DJGHSJBYKIQHIK-UHFFFAOYSA-N |
| Smiles |
C1=C(C=C(C=C1C)C)B(O)O |
| EC No. | 605-655-1 |
| MDL No. | MFCD00185689 |
| PubChem CID | 2734349 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3,5-Dimethylphenylboronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under 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 3,5-dimethylphenyl fragment into larger molecular structures. Because the methyl groups occupy the meta-positions relative to the boronic acid functionality, they provide electronic and steric modification without directly occupying either adjacent ortho-position.
Applications in Medicinal Chemistry
In medicinal chemistry, 3,5-Dimethylphenylboronic acid serves as a building block for preparing aromatic research molecules containing a dimethyl-substituted phenyl group. Methyl substituents can influence molecular lipophilicity, conformational preferences, and interactions with biological targets. Through suitable cross-coupling reactions, researchers can incorporate this aromatic fragment into candidate compounds and evaluate how the substitution pattern affects molecular properties. These applications support lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
3,5-Dimethylphenylboronic acid may support pharmaceutical intermediate synthesis requiring substituted aromatic structures. The boronic acid group enables the formation of carbon–carbon bonds with suitable coupling partners, providing access to biaryl and heteroaryl-containing intermediates. Its symmetrical methyl substitution pattern can simplify certain structural design considerations and provide a consistent aromatic fragment for multistep synthesis. The resulting compounds may undergo further chemical modification depending on the target molecular structure.
Applications in Functionalized Biaryl Synthesis
This compound is particularly useful for constructing biaryl molecules containing a 3,5-dimethylphenyl unit. The boronic acid functionality enables coupling with various aromatic partners, producing substituted biphenyls and heterobiaryls. The methyl substituents can influence molecular packing, hydrophobic interactions, and electronic characteristics. These features make the compound relevant to the preparation of structurally defined aromatic intermediates and the investigation of molecular structure–property relationships.
