(2-acetylphenyl)boronic acid

• ChemBase ID: 32617
• Molecular Formular: C8H9BO3
• Molecular Mass: 163.96626
• Monoisotopic Mass: 164.06447455
• SMILES: c1ccc(c(c1)B(O)O)C(=O)C
• Canonical SMILES: CC(=O)c1ccccc1B(O)O
• InChI: InChI=1S/C8H9BO3/c1-6(10)7-4-2-3-5-8(7)9(11)12/h2-5,11-12H,1H3
• InChIKey: ZKAOVABYLXQUTI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-acetylphenyl)boronic acid
• IUPAC Traditional name: 2-acetylphenylboronic acid
• Synonyms: 2-Acetylphenylboronic acid; 2'-Boronoacetophenone; 1-(2-Boronophenyl)ethan-1-one; 2-Acetylbenzeneboronic acid; 2-Acetylbenzeneboronic acid; 2-Acetylphenylboronic acid; 2-Acetylphenylboronic acid; 2-Acetylbenzeneboronic acid; 2-乙酰苯基硼酸; 2-乙酰基苯硼酸

Database IDs

• CAS Number: 308103-40-4
• MDL Number: MFCD01321263
• PubChem SID: 24870684; 160995924
• PubChem CID: 2734309

CALCULATED PROPERTIES

• Acid pKa: 8.3530245
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.94769454
• LogD (pH = 7.4): 0.9026507
• Log P: 0.9483
• Molar Refractivity: 41.0063 cm^3
• Polarizability: 17.270586 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 170 °C (dec.)(lit.); 170(dec.)°C; ca 170°C dec.

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold/Store under Argon
• 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: 97%; 98%
• Linear Formula: CH3COC6H4B(OH)2

DETAILS

Sigma Aldrich - 470805

Other Notes
Contains varying amounts of anhydride
Packaging
5, 25 g in glass bottle
Application
Reactant involved in:
• Suzuki-Miyaura cross-coupling reactions1
• Rhodium-catalyzed annulation of ynamides2
• Transient masking of hydroxy groups3
• Cationic palladium complex-catalyzed diastereoselective tandem annulation4
• Hydrogen peroxide mediated formation of heteroaryl ethers5
• Copper-catalyzed transmetalation and homocoupling6