Description

4-Amino-3-nitrophenylboronic acid (CAS No. 89466-07-9) is a high-purity boronic acid derivative with the molecular formula C₆H₇BN₂O₄. This compound features a boronic acid functional group attached to a phenyl ring substituted with an amino group and a nitro group at the 4- and 3-positions, respectively. It is widely utilized in organic synthesis, pharmaceutical research, and materials science due to its versatile reactivity as a boronic acid. The product is supplied as a fine powder with ≥95% purity (HPLC), ensuring consistency for sensitive applications. Ideal for Suzuki-Miyaura cross-coupling reactions, this reagent is packaged under inert conditions to maintain stability and shelf life. Suitable for researchers and industrial chemists seeking reliable building blocks for complex molecular architectures.

Properties

• CAS Number: 89466-07-9
• Complexity: 196
• IUPAC Name: (4-amino-3-nitro-phenyl)boronic acid
• InChI: InChI=1S/C6H7BN2O4/c8-5-2-1-4(7(10)11)3-6(5)9(12)13/h1-3,10-11H,8H2
• InChI Key: IRTXQNNJQZNKRP-UHFFFAOYSA-N
• Exact Mass: 182.0498869
• Molecular Formula: C6H7BN2O4
• Molecular Weight: 181.94
• SMILES: B(C1=CC(=C(C=C1)N)[N+](=O)[O-])(O)O
• Topological: 112
• Monoisotopic Mass: 182.0498869
• Synonyms: 4-Amino-3-nitrophenylboronic acid, 89466-07-9, 4-Amino-3-nitrophenylboronicacid, (4-amino-3-nitrophenyl)boronic acid, MFCD07437851, SCHEMBL854057, DTXSID10584649, IRTXQNNJQZNKRP-UHFFFAOYSA-N, AKOS015854756, AKOS015894333, AB41937, AS-53686, DB-016053, CS-0174691, P16879, 4-Amino-3-nitrophenylboronic acid, technical grade, 90%, 4-Amino-3-nitrophenylboronic acid(contains varying amounts of Anhydride)

Application

4-Amino-3-nitrophenylboronic acid is primarily used as a key intermediate in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl compounds. Its boronic acid group enables efficient palladium-catalyzed coupling with aryl halides, making it valuable in pharmaceutical and agrochemical development. The nitro and amino substituents further allow for selective functionalization, aiding in the creation of dyes, sensors, and advanced materials. Researchers also employ it in the design of boron-containing therapeutics and as a ligand in catalysis.

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