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431966 Sigma-Aldrich

4-Formylphenylboronic acid

≥95.0%

Synonym: 4-(Dihydroxyboryl)benzaldehyde, 4-Formylbenzeneboronic acid, 4-Boronobenzaldehyde, p-Formylbenzeneboronic acid, p-Formylphenylboronic acid

  • CAS Number 87199-17-5

  • Linear Formula HCOC6H4B(OH)2

  • Molecular Weight 149.94

  •  Beilstein/REAXYS Number 3030770

  •  MDL number MFCD00151823

  •  PubChem Substance ID 24867058

  •  NACRES NA.22

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Properties

Related Categories Aldehydes, Aryl Boronic Acids, Boronic Acids, Boronic Acids and Derivatives, Building Blocks,
Quality Level   100
assay   ≥95.0%
mp   237-242 °C (lit.)
SMILES string   OB(O)c1ccc(C=O)cc1
InChI   1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
InChI key   VXWBQOJISHAKKM-UHFFFAOYSA-N

Description

Application

4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions and it can be used as a reagent for:
• Palladium-catalyzed Suzuki-Miyaura cross-coupling in water.
• Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides.
• Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.
• Triethylamine-catalyzed three-component Hantzsch condensations.
• Copper-catalyzed nitrations.
• Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta.
• Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides.
• Palladium-catalyzed aerobic oxidative cross-coupling reactions.
• The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.
• The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.
• The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.
• A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes.

Packaging

1, 5, 25 g in glass bottle

Other Notes

Contains varying amounts of anhydride

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
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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