Hangzhou Leap Chem Co., Ltd. is one of the most professional manufacturers and suppliers of (4-boc-aminophenyl)boronic acid丨cas 380430-49-9 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 Inquiry (4-Boc-Aminophenyl)Boronic Acid丨CAS 380430-49-9
(4-Boc-Aminophenyl)boronic acid (CAS 380430-49-9), also known as 4-(tert-butoxycarbonylamino)phenylboronic acid or N-Boc-4-aminophenylboronic acid, is a multifunctional aromatic organoboron compound featuring a boronic acid group and a Boc-protected amino group at the para-positions of a benzene ring. The compound combines the synthetic versatility of an arylboronic acid with the controlled reactivity of a protected aromatic amine. The tert-butoxycarbonyl (Boc) protecting group helps prevent unwanted reactions involving the amino functionality during selected synthetic transformations and can be removed under suitable acidic conditions. These characteristics make (4-Boc-Aminophenyl)boronic acid a useful building block for medicinal chemistry, pharmaceutical intermediate development, Suzuki–Miyaura cross-coupling reactions, functionalized aromatic compound synthesis, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C11H16BNO4/c1-11(2,3)17-10(14)13-9-6-4-8(5-7-9)12(15)16/h4-7,15-16H,1-3H3,(H,13,14) |
| InChI Key | UBVOLHQIEQVXGM-UHFFFAOYSA-N |
| Smiles | C1=C(NC(OC(C)(C)C)=O)C=CC(=C1)B(O)O |
| EC No. | 670-415-5 |
| MDL No. | MFCD02093054 |
| PubChem CID | 3613184 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(4-Boc-Aminophenyl)boronic acid is particularly useful in Suzuki–Miyaura cross-coupling reactions for constructing substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation enables the introduction of a Boc-protected aminophenyl fragment into more complex molecular frameworks. The protected amino group may remain intact under suitable coupling conditions, allowing subsequent deprotection and further functionalization. This approach is valuable for preparing amino-substituted aromatic intermediates while reducing unwanted reactions involving an unprotected amino group.
Applications in Medicinal Chemistry
In medicinal chemistry, (4-Boc-Aminophenyl)boronic acid serves as a building block for preparing nitrogen-containing aromatic compounds and investigating structure–activity relationships. Aminophenyl fragments are frequently incorporated into pharmaceutical research molecules because amino functionality can support hydrogen-bonding interactions and provide opportunities for additional structural modification. The Boc protecting group allows researchers to introduce the aromatic fragment through suitable coupling reactions before exposing the amino group for further transformations. This controlled synthetic approach supports lead optimization, analog synthesis, and the development of structurally diverse compound libraries.
Applications in Pharmaceutical Intermediate Synthesis
(4-Boc-Aminophenyl)boronic acid may support pharmaceutical research programs requiring intermediates containing a para-substituted aminophenyl framework. The boronic acid functionality enables carbon–carbon bond formation with compatible aromatic or heteroaromatic coupling partners, while the Boc-protected amino group provides a latent reactive site. After the desired aromatic framework has been constructed, the Boc group can be removed under suitable conditions to generate a free amino functionality. The resulting aromatic amine may undergo selected acylation, sulfonylation, urea formation, or other chemical transformations. This combination of functional groups provides flexibility for developing multistep synthetic routes and preparing advanced pharmaceutical research intermediates.
Applications in Protected Amino Group Chemistry
The Boc-protected amino functionality makes (4-Boc-Aminophenyl)boronic acid useful in synthetic strategies requiring temporary protection of an aromatic amine. The Boc group can help control chemoselectivity by limiting reactions at the nitrogen atom during selected transformations involving the boronic acid group. Following the desired coupling or molecular modification, the protecting group may be removed to provide an amino-substituted aromatic product. Researchers can use this approach to investigate protecting-group compatibility, reaction sequence optimization, and the preparation of multifunctional aromatic compounds. Because boronic acids may exhibit sensitivity to certain reaction conditions, protection and deprotection procedures should be evaluated for compatibility with the complete molecular structure.
