153853-43-1

Basic information

• Product Name: 3-propionamidophenylboronic acid
• Synonyms: 3-propionamidophenylboronic acid
• CAS NO: 153853-43-1
• Molecular Formula: C₉H₁₂BNO₃
• Molecular Weight: 193.01
• Mol File: 153853-43-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.19g/cm³
• Refractive Index: 1.545
• PKA: 7.93±0.19(Predicted)
• CAS DataBase Reference: 3-propionamidophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-propionamidophenylboronic acid(153853-43-1)
• EPA Substance Registry System: 3-propionamidophenylboronic acid(153853-43-1)

Safety Data

• Hazardous Substances Data: 153853-43-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H12BNO3/c1-2-9(12)11-8-5-3-4-7(6-8)10(13)14/h3-6,13-14H,2H2,1H3,(H,11,12)

Upstream product

• 30418-59-8 3-Aminophenylboronic acid 
• 79-03-8 propionyl chloride 
• 802294-64-0 propionic acid 
• 206658-89-1 3-aminobenzeneboronic acid monohydrate 

Downstream Products

• 620-71-3 N-(phenyl)-2-methylacetamide 

Relevant articles and documents

Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid (Neu5Ac) in aqueous solution with varying pH

Borates are known to interact with carbohydrate moieties expressed on the surface of biological membranes of a variety of cells, viruses, bacteria, and fungi. This study revealed the anomalous binding profile of borate in aqueous solution with N-acetylneuraminic acid (Neu5Ac, sialic acid) as a potential receptor site on the surfaces of biological membranes using 11B, 1H, 13C, and 15N nuclear magnetic resonance spectroscopies. 3-(Propionamido)phenylboronic acid (PAPBA) was chosen as the model borate compound. The equilibrium constant (K) for Neu5Ac binding to PAPBA was compared with those for glucose, mannose, and galactose, which are the major carbohydrate constituents of glycoproteins and glycolipids expressed on biological membranes. In the Neu5Ac/PAPBA system, the unusual pH dependency of the K values, a decrease in K with increasing pH, was observed, suggesting the formation of a trigonal-formed complex stabilized by the coordination of an amide group of Neu5Ac at the C-5 position to the boron atom, forming intramolecular B-N or B-O bonding. Furthermore, the anomalously high complexing ability at physiological pH 7.4 was confirmed for this system, with the K value 37.6 which is approximately 7 times higher than that for glucose. This exceptionally high value of K at physiological pH, compared to those of other sugars, strongly suggests that the boronic acid selectively recognizes the Neu5Ac residues of the glycosylated components including glycoproteins and gangliosides existing on the surface of the biological membranes.

Preparation and uses of conjugated solid supports for boronic acids

The invention provides novel solid supports comprising dihydroxyalkyl aminoalkyl and dihydroxyalkylaminobenzyl groups, and methods for making and using them. The supports are particularly useful for immobilizing and derivatizing functionalized boronic acids for use in solid phase synthesis, such as those used in combinatorial chemistries. The compositions and methods of the invention are also useful as scavenger solid supports, e.g., in solution-phase parallel synthesis of small molecule libraries, and for use in resin-to-resin transfer reactions via phase transfer of solid supported boronic acids under both aqueous and anhydrous conditions. The methods of the invention provide convergent solid-phase synthesis of symmetrically or unsymmetrically functionalized compounds, such as biphenyl compounds. Also provided are synthesizer devices, e.g., semiautomated parallel synthesizers.

Boronate linker for 'traceless' solid-phase synthesis

The development of a new boron-based strategy for 'traceless' solid- phase synthesis of aromatic compounds is reported. A resin capture process can precede the cleavage step.