470821

4-Acetylphenylboronic acid

95%

• Linear Formula: CH₃COC₆H₄B(OH)₂
• CAS Number: 149104-90-5
• Molecular Weight: 163.97
• MDL number: MFCD01074667
• UNSPSC Code: 12352103
• PubChem Substance ID: 24870686
• NACRES: NA.22

Properties

• Assay: 95%
• mp: 240-244 °C (lit.)
• SMILES string: CC(=O)c1ccc(cc1)B(O)O
• InChI: 1S/C8H9BO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5,11-12H,1H3
• InChI key: OBQRODBYVNIZJU-UHFFFAOYSA-N

Description

General description

4-Acetylphenylboronic acid is a boronate, belongs to a class of synthetic organic compounds. It reacts rapidly with peroxynitrite (ONOO(-)) to form stable hydroxy derivatives. It undergoes Suzuki coupling with 4-bromotriphenylamine catalyzed by dichlorobis(triphenylphosphine)Pd(II), during the synthesis of dendrimers.

Application

4-Acetylphenylboronic acid was used in the synthesis of 4′-azidoacetophenone.

Reactant involved in:

• Palladium-catalyzed decarboxylative coupling
• Copper-catalyzed hydroxylation
• Palladium-catalyzed Suzuki-Miyaura cross-coupling
• Cross-coupling with α-bromocarbonyl compounds
• Oxidation catalyzed by Baeyer-Villiger monooxygenases
• 1,5-substitution reactions

Other Notes

Contains varying amounts of anhydride

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves