677746-32-6

Basic information

• Product Name: Boronic acid, (2-hydroxy-5-nitrophenyl)-
• CAS NO: 677746-32-6
• Molecular Formula: C6H6BNO5
• Mol File: 677746-32-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Boronic acid, (2-hydroxy-5-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Boronic acid, (2-hydroxy-5-nitrophenyl)-(677746-32-6)
• EPA Substance Registry System: Boronic acid, (2-hydroxy-5-nitrophenyl)-(677746-32-6)

Safety Data

• Hazardous Substances Data: 677746-32-6(Hazardous Substances Data)

Upstream product

• 677746-34-8 2-(2-methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 677746-35-9 2-methoxy-5-nitrophenylboronic acid 
• 5197-28-4 2-bromo-4-nitroanisole 

Relevant articles and documents

The Design of Boronic Acid Spectroscopic Reporter Compounds by Taking Advantage of the pKa-Lowering Effect of Diol Binding: Nitrophenol-Based Color Reporters for Diols

The complex that forms between a boronic acid and a diol is often much more acidic than the starting boronic acid. In conditions where the solution pH is between the two pKa values, the boron atom will convert from a neutral trigonal form to an anionic tetrahedral form upon complexation. Such a change is likely to dramatically alter the electron density of neighboring groups. Utilizing this effect, we have designed and synthesized two nitrophenol-based boronic acid reporter compounds that change ionization states and therefore spectroscopic properties upon diol binding. Both compounds show significant UV changes upon addition of saccharides. For example, a blue shift of the absorption max from 373 to 332 nm was observed with the addition of D-fructose to 2-hydroxy-5-nitrophenylboronic acid at neutral pH. Such a reporter compound can be used as a recognition and signaling unit for the construction of polyboronic acid sensors for the selective and specific recognitions of saccharides of biological significance.