(4-acetylphenyl)boronic acid

• ChemBase ID: 8349
• Molecular Formular: C8H9BO3
• Molecular Mass: 163.96626
• Monoisotopic Mass: 164.06447455
• SMILES: c1c(ccc(c1)B(O)O)C(=O)C
• Canonical SMILES: OB(c1ccc(cc1)C(=O)C)O
• InChI: InChI=1S/C8H9BO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5,11-12H,1H3
• InChIKey: OBQRODBYVNIZJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-acetylphenyl)boronic acid
• IUPAC Traditional name: 4-acetylphenylboronic acid
• Synonyms: 4-Acetylphenylboronic acid; 4-Acetylbenzeneboronic acid 96%; 4-Acetylphenylboronic acid; 4'-Boronoacetophenone; 4-Acetylbenzeneboronic acid; 1-[4-(dihydroxyboranyl)phenyl]ethan-1-one; 4-Acetylphenylboronic acid; 4-乙酰苯基硼酸; 4-乙酰基苯硼酸

Database IDs

• CAS Number: 149104-90-5
• EC Number: 000-000-0
• MDL Number: MFCD01074667
• Beilstein Number: 7869162
• PubChem SID: 24870686; 160971656
• PubChem CID: 3702122

CALCULATED PROPERTIES

• Acid pKa: 8.57704
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.94793844
• LogD (pH = 7.4): 0.9204773
• Log P: 0.9483
• Molar Refractivity: 41.0063 cm^3
• Polarizability: 17.269312 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 240-244 °C(lit.); 256-260°C; 258°C(dec); ca 240°C dec.
• Hydrophobicity(logP): 1.034

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%; 98%
• Linear Formula: CH3COC6H4B(OH)2

DETAILS

Sigma Aldrich - 470821

Other Notes
Contains varying amounts of anhydride
Packaging
5, 25 g in glass bottle
Application
Reactant involved in:
• Palladium-catalyzed decarboxylative coupling1
• Copper-catalyzed hydroxylation2
• Palladium-catalyzed Suzuki-Miyaura cross-coupling3
• Cross-coupling with α-bromocarbonyl compounds4
• Oxidation catalyzed by Baeyer-Villiger monooxygenases5
• 1,5-substitution reactions6