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2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS 191171-55-8), also known as 2-aminophenylboronic acid pinacol ester, is a multifunctional aromatic organoboron compound containing an amino group and a pinacol boronate ester group at adjacent positions on a benzene ring. Its structure combines the synthetic versatility of a protected boronic acid with the chemical reactivity of an aromatic amine. The boronate ester group enables carbon–carbon bond formation through suitable cross-coupling reactions, while the amino group provides opportunities for condensation, acylation, and heterocyclic ring formation. These characteristics make the compound a useful building block for medicinal chemistry, pharmaceutical intermediate synthesis, heterocyclic chemistry, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C12H18BNO2/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8H,14H2,1-4H3 |
| InChI Key | ZCJRWQDZPIIYLM-UHFFFAOYSA-N |
| Smiles | CC1(C)OB(OC1(C)C)C1=CC=CC=C1N |
| EC No. | 626-344-7 |
| MDL No. | MFCD02179448 |
| PubChem CID | 2734652 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, the pinacol boronate ester group can react with compatible aryl or heteroaryl halides to form new carbon–carbon bonds. This transformation enables the introduction of an ortho-aminophenyl fragment into larger molecular frameworks. The amino group may be retained for subsequent transformations, although its potential interaction with catalysts and other reagents should be considered during reaction optimization.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing aromatic research molecules containing amino functionality. The amino group can participate in hydrogen-bonding interactions and provides a useful site for structural modification. Through cross-coupling reactions, researchers can incorporate the ortho-aminophenyl fragment into diverse molecular frameworks. Subsequent functionalization of the amino group enables the preparation of amides, sulfonamides, and other nitrogen-containing derivatives for lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline may support pharmaceutical intermediate synthesis involving multifunctional aromatic structures. The boronate ester group provides a route for constructing carbon–carbon bonds, while the amino group can undergo selected reactions such as acylation, condensation, and nitrogen functionalization. These complementary functionalities allow chemists to design multistep synthetic routes with controlled modification of different positions on the aromatic ring. The compound is particularly useful when a target intermediate requires an amino group adjacent to a newly formed aromatic linkage.
Applications in Nitrogen-Containing Heterocyclic Synthesis
The ortho-amino substitution pattern makes this compound especially relevant to heterocyclic synthesis. Following suitable cross-coupling reactions, the amino group can participate in intramolecular cyclization or condensation reactions when compatible functional groups are present. Such strategies may provide access to substituted indoles, benzimidazoles, quinolines, and other nitrogen-containing heterocyclic frameworks, depending on the selected reaction partners and synthetic conditions. These structural classes are widely investigated in pharmaceutical and specialty chemical research.
