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Phenylboronic acid

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Phenylboronic acid Basic information

Product Name:
Phenylboronic acid
Synonyms:
  • phenyboronic
  • phenyl-boronicaci
  • phenyldihydroxyborane
  • t-500
  • usafbo-2
  • Phenylboronic Acid (contains varying amounts of Anhydride)
  • Benzenboronic acid
  • Phenylboric Acid: (Benzeneboronic acid)
CAS:
98-80-6
MF:
C6H7BO2
MW:
121.93
EINECS:
202-701-9
Product Categories:
  • Aryl Boronic Acids
  • Boronic Acids and Derivatives
  • Chemical Synthesis
  • Organometallic Reagents
  • Unsubstituted Aryl Boronic Acids
  • OLED materials,pharm chemical,electronic
  • Aryl
  • Organoborons
  • Analytical Chemistry
  • B (Classes of Boron Compounds)
  • Boronic Acid, etc. (GC Derivatizing Reagents)
  • Boronic Acids
  • Boronate Ester
  • Potassium Trifluoroborate
  • Boron compounds
  • blocks
  • BoronicAcids
  • Boronic Acid series
  • PHARMACEUTICAL INTERMEDIATES
  • Substituted Boronic Acids
  • Organometallics
  • Boronic Acid
  • GC Derivatizing Reagents
  • organic or inorganic borate
  • bc0001
  • 98-80-6
Mol File:
98-80-6.mol
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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. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
8.83(at 25℃)
form 
Crystalline Powder
color 
White to off-white
Water Solubility 
10 g/L (20 ºC)
Sensitive 
Hygroscopic
Merck 
14,1068
BRN 
970972
Stability:
Hygroscopic
InChIKey
HXITXNWTGFUOAU-UHFFFAOYSA-N
CAS DataBase Reference
98-80-6(CAS DataBase Reference)
EPA Substance Registry System
Boronic acid, phenyl- (98-80-6)
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Safety Information

Hazard Codes 
Xn,Xi,N
Risk Statements 
22-36/37/38-20/21/22
Safety Statements 
22-24/25-36/37/39-26-36
WGK Germany 
3
RTECS 
CY8575000
Hazard Note 
Harmful
TSCA 
Yes
HazardClass 
IRRITANT, MOISTURE SENSITIVE
HS Code 
29310095
Toxicity
LD50 orl-rat: 740 mg/kg 14KTAK -,693,64

MSDS

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Phenylboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

Reagent 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 •

Uses

suzuki reaction

Uses

Phenylboronic 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

Uses

Phenylboronic 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

General Description

Phenylboronic acid (PBA) is an organoboronic acid. It behaves as a molecular receptor that can attach to compounds containing cis-diol group. Microwave-assisted Suzuki coupling of aryl chlorides with phenylboronic acid in the presence of Pd/C (catalyst) and water (solvent) has been described. Palladium-catalyzed cross-coupling reaction of phenylboronicacid with haloarenes to afford biaryls has been reported.

Safety Profile

Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.Mildly toxic by skin contact. When heated to decomposition it emitsacrid smoke and irritating fumes.

Phenylboronic acidSupplier

Jiangsu Aikon Biopharmaceutical R&D co.,Ltd. Gold
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