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78181 Sigma-Aldrich

Phenylboronic acid

purum, ≥97.0% (HPLC)

Synonym: Benzeneboronic acid, Dihydroxyphenylborane, NSC 66487, Phenyl-boric acid, Phenylboric acid, Phenyldihydroxyborane

  • CAS Number 98-80-6

  • Linear Formula C6H5B(OH)2

  • Molecular Weight 121.93

  •  Beilstein Registry Number 970972

  •  EC Number 202-701-9

  •  MDL number MFCD00002103

  •  PubChem Substance ID 329768124

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Properties

Related Categories Aryl Boronic Acids, Boronic Acids, Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents,
InChI Key   HXITXNWTGFUOAU-UHFFFAOYSA-N
grade   purum
assay   ≥97.0% (HPLC)
mp   216-219 °C(lit.)
  218-222 °C

Description

Other Notes

Contains varying amounts of phenylboronic anhydride

Packaging

1 g in glass bottle

10 g in poly bottle

50 g in glass bottle

Application

Phenylboronic acid may be employed in the following reactions:
• Rhodium-catalyzed intramolecular amination.
• Pd-catalyzed direct arylation.
• Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles.
• Palladium-catalyzed stereoselective Heck-type reaction.
• Highly effective Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water.

Phenylboronic acid may be employed as reagent in the preparation of:
• Ni(II) pincer complex and Pd(II) pyridoxal hydrazone metallacycles as catalysts for the Suzuki-Miyaura cross-coupling reactions.
• N-type polymers for all-polymer solar cells.
• Novel series of potent and selective mTOR kinase inhibitors.
• Inhibitors of lactate dehydrogenase against cancer cell proliferation.

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.

Price and Availability


Laboratory Gloves

KitAlysis - Increasing Catalysis Productivity

Cross-Coupling Guide
Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
CY8575000

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

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