431966

4-Formylphenylboronic acid

≥95.0%

• Synonym(s): 4-(Dihydroxyboryl)benzaldehyde, 4-Boronobenzaldehyde, 4-Formylbenzeneboronic acid, p-Formylbenzeneboronic acid, p-Formylphenylboronic acid
• Linear Formula: HCOC₆H₄B(OH)₂
• CAS Number: 87199-17-5
• Molecular Weight: 149.94
• Beilstein/REAXYS Number: 3030770
• MDL number: MFCD00151823
• UNSPSC Code: 12352103
• PubChem Substance ID: 24867058
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: ≥95.0%
• mp: 237-242 °C (lit.)
• functional group: aldehyde
• 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.

Other Notes

Contains varying amounts of anhydride

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H317
• pcodes: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Hazard Classifications: Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges