ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Boric acid > Phenylboronic acid
Phenylboronic acid Chemical Properties
- Melting point:216-219 °C(lit.)
- Boiling point:265.9±23.0 °C(Predicted)
- Density 1.13±0.1 g/cm3(Predicted)
- storage temp. 0-6°C
- pka8.83(at 25℃)
- form Crystalline Powder
- color White to off-white
- Water Solubility 10 g/L (20 ºC)
- Sensitive Hygroscopic
- Merck 14,1068
- BRN 970972
- CAS DataBase Reference98-80-6(CAS DataBase Reference)
- EPA Substance Registry SystemBoronic acid, phenyl- (98-80-6)
Phenylboronic acid Usage And Synthesis
- Chemical Propertieswhite to light yellow crystal powder
- UsesReagent used for• ;Rhodium-catalyzed intramolecular amination1 • ;Pd-catalyzed direct arylation2 • ;Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles3 • ;Palladium-catalyzed stereoselective Heck-type reaction4 • ;Highly effective Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water5 Reagent used in Preparation of• ;Ni(II) pincer complex and Pd(II) pyridoxal hydrazone metallacycles as catalysts for the Suzuki-Miyaura cross-coupling reactions6,7• ;N-type polymers for all-polymer solar cells8 •
- Usessuzuki reaction
- UsesPhenylboronic Acid is a compound used in organic synthesis of various pharmaceutical goods.
Phenylboronic acid (PBA) and its derivatives can bind sugars and other diol compounds to form cyclic boronate esters. These esters bear negative charges. Due to this reaction, sugars can be detected by means of electrochemical and optical techniques.
PBA modified electrodes have been constructed as reagentless electrochemical sensors. There, PBA is absorbed on the electrode surface either as a self- assembled monolayer film ore a polymer thin film. Basically, for optical detection techniques for the detection of sugars, PBA is modified with a chromophore that should change its properties on reaction with a sugar.
Reaction of Phenylboronic acid with a sugar
- UsesPhenylboronic acid and its derivatives form complexes with polyol compounds such as saccharides and poly(vinyl alcohol) (PVA). Glucose-sensitive hydrogels can be prepared by using phenylhoronic acid as a ligand for target glucose. For example. a copolymer with phenylboronic acid moieties was synthesized by copolymerization of 4V-vinyl-2-pyrrolidone (NVP) and 3-(acryl- amide)phcnylhoronic acid (PBA). The complexes between the NVP-PBA copolymer and PVA enable us to construct glucose-sensitive insulin release systems because the complexes dissociated in response to the glucose concentration.
This phenylboronic acid is soluble in water and the coupling reaction can even be carried out in water. It is compatible with many organic substituents such as esters, ketones, alcohols, etc. which would prohibit the use of Grignard reagents in coupling reactions.
- Synthesis Reference(s)Organic Syntheses, Coll. Vol. 4, p. 68, 1963
The Journal of Organic Chemistry, 49, p. 5237, 1984 DOI: 10.1021/jo00200a045
- Safety ProfilePoison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.Mildly toxic by skin contact. When heated to decomposition it emitsacrid smoke and irritating fumes.
Phenylboronic acid Preparation Products And Raw materials
- 2-PHENYL-1,3,2-DIOXABORINANE PeraMpanel PeraMpanel 6'-Methoxy-2,3'-bipyridine 3,5-Dibromopyridine PeraMpanel PeraMpanel PeraMpanel 2-Cyanophenylboronic acid 3,5-Dimethoxypyridine 1-Phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one PRMWGUBFXWROHD-MYWHSQMISA-N 2-Bromobenzonitrile 2-(2-cyanophenyl)benzonitrile 5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE 2,5-Dibromopyridine 5-Bromo-2-methoxypyridine 2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
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- Nov 12，2019