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Procurement (Pyrimidin-5-yl)boronic acid丨CAS 109299-78-7
(Pyrimidin-5-yl)boronic acid (CAS 109299-78-7), also known as pyrimidine-5-boronic acid, is a heteroaryl organoboron compound featuring a boronic acid group attached to the 5-position of a pyrimidine ring. The pyrimidine structure contains two nitrogen atoms, providing distinctive electronic and hydrogen-bond-accepting properties. Combined with the versatile boronic acid functionality, this compound is a valuable building block for pharmaceutical intermediate synthesis, medicinal chemistry, heterocyclic compound development, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C4H5BN2O2/c8-5(9)4-1-6-3-7-2-4/h1-3,8-9H |
| InChI Key | HZFPPBMKGYINDF-UHFFFAOYSA-N |
| Smiles | C1=NC=C(B(O)O)C=N1 |
| EC No. | 673-929-8 |
| MDL No. | MFCD03002366 |
| PubChem CID | 2795193 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(Pyrimidin-5-yl)boronic acid is a useful heteroaryl coupling partner in Suzuki–Miyaura cross-coupling reactions. Under suitable palladium-catalyzed conditions, it can react with compatible aryl or heteroaryl halides to form carbon–carbon bonds, enabling the preparation of substituted pyrimidines and biheteroaryl compounds. These transformations provide access to complex nitrogen-containing molecular frameworks for pharmaceutical and materials research.
Applications in Pharmaceutical Intermediate Synthesis
Pyrimidine derivatives are important structural components in many pharmaceutical compounds. (Pyrimidin-5-yl)boronic acid provides a convenient synthetic route for introducing a pyrimidinyl group into aromatic and heteroaromatic frameworks. Its coupling chemistry supports the preparation of advanced intermediates for multistep synthesis, particularly when the target structure requires a nitrogen-rich heterocyclic ring.
Applications in Medicinal Chemistry
In medicinal chemistry, the pyrimidine ring is widely used as a molecular building block because its nitrogen atoms can participate in hydrogen-bond-accepting interactions and influence molecular polarity. (Pyrimidin-5-yl)boronic acid enables researchers to incorporate this heterocyclic motif into candidate molecules through cross-coupling reactions. It is useful in analog synthesis, lead optimization, and structure–activity relationship studies.
Applications in Heterocyclic Compound Synthesis
This compound is valuable for constructing substituted pyrimidine derivatives and more complex fused or linked heterocyclic structures. The boronic acid group provides a functional handle for coupling with suitable organic halides, allowing the pyrimidine ring to be connected with other heteroaromatic systems. Such transformations support the development of structurally diverse compounds for pharmaceutical and chemical research.
