3-tert-Butoxycarbonylphenylboronic acid CAS: 220210-56-0
Catalog Number | XD93445 |
Product Name | 3-tert-Butoxycarbonylphenylboronic acid |
CAS | 220210-56-0 |
Molecular Formula | C11H15BO4 |
Molecular Weight | 222.05 |
Storage Details | Ambient |
Product Specification
Appearance | White powder |
Assay | 99% min |
3-tert-Butoxycarbonylphenylboronic acid, also known as Boc-phenylboronic acid, is an important boronic acid derivative with significant applications in organic synthesis and medicinal chemistry.One of the primary uses of 3-tert-Butoxycarbonylphenylboronic acid is as a protecting group in organic synthesis. The tert-butyloxycarbonyl (BOC) group is commonly employed to temporarily protect amine functional groups during various reactions. By attaching the BOC group to the amine moiety, the reactivity of the amine is attenuated, allowing for selective reactions at other positions on the molecule. The BOC group can be easily removed under mild conditions, thus revealing the original amine functionality. This protecting group strategy enables efficient synthesis of complex organic molecules, such as pharmaceuticals and natural products.Furthermore, 3-tert-Butoxycarbonylphenylboronic acid serves as a valuable reagent for carbon-carbon bond formation. Boronic acids, including Boc-phenylboronic acid, readily form boronate esters when reacted with nucleophiles, such as alcohols or amines. These boronate esters can then undergo a variety of transformations, including Suzuki-Miyaura cross-coupling reactions, Negishi couplings, and Stille couplings. These reactions enable the formation of complex organic molecules with diverse substitution patterns and functional groups. Boc-phenylboronic acid is particularly useful for introducing the phenylboronic acid moiety into target molecules.Additionally, Boc-phenylboronic acid plays a crucial role in medicinal chemistry. The boronic acid functionality can selectively interact with diols or boronate ester-sensitive functional groups in biological targets, enabling the design of boronate-based enzyme inhibitors and receptor ligands. Boc-phenylboronic acid can be incorporated into small-molecule inhibitors, peptides, or prodrugs to impart desired properties or enhance target specificity. These boronate-based compounds have shown promise in the treatment of various diseases, including cancer, diabetes, and inflammation.In summary, 3-tert-Butoxycarbonylphenylboronic acid, or Boc-phenylboronic acid, finds diverse applications in organic synthesis and medicinal chemistry. Its BOC group serves as a protecting group, allowing for selective reactions at other positions on the molecule. Furthermore, the boronic acid functionality enables carbon-carbon bond formations, facilitating the synthesis of complex organic molecules. Additionally, Boc-phenylboronic acid plays a vital role in medicinal chemistry, where it is used in the design of boronate-based enzyme inhibitors and receptor ligands. Overall, Boc-phenylboronic acid is a valuable reagent that contributes to advancements in synthetic chemistry and drug discovery research.