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521418 Sigma-Aldrich

4-Cyanophenylboronic acid

≥95%

Synonym: (p-Cyanophenyl)boronic acid, 4-Cyanobenzeneboronic acid, 4-Cyanophenylboric acid

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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   ≥95%
mp   >350 °C (lit.)
SMILES string   OB(O)c1ccc(cc1)C#N
InChI   1S/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H
InChI key   CEBAHYWORUOILU-UHFFFAOYSA-N

Description

Application

Reactant involved in:
• Oxidative hydroxylation
• Trifluoromethylation
• 1,4-Addition reactions

Precursor in the synthesis of inhibitors such as:
• Tpl2 kinase inhibitors
• P2X7 antagonists used in the treatment of pain

Reagent used for
• Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water
• Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines with arylboronates
• Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids
• Ferric perchlorate-promoted reaction of fullerenes with various arylboronic acids to give fullerenyl boronic esters
• Phosphine-free Suzuki-Miyaura cross-coupling
• Palladacycles as effective catalysts for multicomponent reaction with allylpalladium-intermediates
• Chan-Lam-type Cu-catalyzed S-arylation of thiols
• Regioselective cross-coupling reactions under modfied Suzuki and Still cross-coupling reactions with Copper catalysis
• Metal-free biaryl coupling in dimethyl carbonate as a solvent

Reagent used for Preparation of
• Himbacine analogs as thrombin receptor antagonists and potential antiplatelet agents
• Trisulfonated calixarene upper-rim sulfonamido and their complexation with trimethyllysine epigenetic mark
• Antimalarial compounds via Suzuki cross-coupling
• Deoxyuridine derivatives

Packaging

1 g in glass bottle

10 g in poly bottle

Other Notes

Contains varying amounts of anhydride

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
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

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

Peer-Reviewed Papers
15

References

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