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393622 Sigma-Aldrich

p-Tolylboronic acid

97%

Synonym: (p-Methylphenyl)boronic acid, 4-Methylbenzeneboronic acid, 4-Methylphenylboronic acid, 4-Tolueneboronic acid, 4-Tolylboronic acid, p-Tolueneboronic acid, NSC 62870, p-Methylbenzeneboronic acid

  • CAS Number 5720-05-8

  • Linear Formula CH3C6H4B(OH)2

  • Molecular Weight 135.96

  •  Beilstein/REAXYS Number 2935970

  •  MDL number MFCD00039138

  •  PubChem Substance ID 24864529

  •  NACRES NA.22

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Properties

Related Categories Aryl Boronic Acids, Boronic Acids, Boronic Acids and Derivatives, Chemical Synthesis, Monosubstituted Aryl Boronic Acids,
Quality Level   100
assay   97%
mp   256-263 °C (lit.)
SMILES string   Cc1ccc(cc1)B(O)O
InChI   1S/C7H9BO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5,9-10H,1H3
InChI key   BIWQNIMLAISTBV-UHFFFAOYSA-N

Description

Application

Reagent used for
• Palladium (Pd)-catalyzed direct arylation
• Direct Palladium(II)-Catalyzed Synthesis
• Palladium-catalyzed arylation by Suzuki-Miyaura cross-coupling in water
• Cyclopalladation
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence
• Ruthenium catalyzed direct arylation
• Rhodium-catalyzed asymmetric conjugate addition
• Ligand-free copper-catalyzed cross-coupling reactions
• Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions
• Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions

Reagent used in Preparation of
• Catalysts for Suzuki-Miyaura cross-coupling of aryl bromides
• Recyclable Palladium nanoparticle catalysts immobilized by click ionic copolymers as for Suzuki-Miyaura cross-coupling reactions in water

Packaging

1, 10 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
XS7400000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Arylboronic Acids

We are pleased to present its complete selection of arylboronic acids, the building blocks of the Suzuki coupling experiment. Most arylboronic acids readily undergo dehydration reactions to give a cy...
ChemFiles 2001, 1.1, 5.
Keywords: Building blocks, Coupling reactions, Dehydration reaction, Suzuki coupling

Boronic Acids - ChemFiles 2007

Most boronic acids readily undergo dehydration reactions to give a cyclic (trimer) anhydride. Our selection of boronic acids may contain varying amounts of this cyclic anhydride. Fortunately, the aci...
ChemFiles 2007, 7.7, 3.
Keywords: Coupling reactions, Dehydration reaction, Suzuki coupling

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Lab Chemicals

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Keywords: Gas chromatography, Infrared spectroscopy, Sublimation, Thin layer chromatography

Peer-Reviewed Papers
15

References

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