(3-acetamidophenyl)boronic acid

• ChemBase ID: 32767
• Molecular Formular: C8H10BNO3
• Molecular Mass: 178.9809
• Monoisotopic Mass: 179.07537359
• SMILES: c1c(B(O)O)cc(cc1)NC(=O)C
• Canonical SMILES: CC(=O)Nc1cccc(c1)B(O)O
• InChI: InChI=1S/C8H10BNO3/c1-6(11)10-8-4-2-3-7(5-8)9(12)13/h2-5,12-13H,1H3,(H,10,11)
• InChIKey: IBTSWKLSEOGJGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-acetamidophenyl)boronic acid
• IUPAC Traditional name: 3-acetamidophenylboronic acid
• Synonyms: 3-Acetylaminophenylboronic acid; 3-Acetamidobenzeneboronic acid; 3-Acetamidobenzeneboronic acid; 3-Acetamidophenylboronic acid; 3-Acetamidophenylboronic acid; 3-Acetamidophenylboronic acid; 3-Acetamidobenzeneboronic acid; 3-乙酰氨基苯硼酸; 3-乙酰胺基苯硼酸; 3-乙酰氨基苯硼酸

Database IDs

• CAS Number: 78887-39-5
• EC Number: 000-000-0
• MDL Number: MFCD00236013
• Beilstein Number: 3278316
• PubChem SID: 24880272; 160996074
• PubChem CID: 157274

CALCULATED PROPERTIES

• Acid pKa: 8.680461
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.965015
• LogD (pH = 7.4): 0.9432268
• Log P: 0.9653
• Molar Refractivity: 45.4665 cm^3
• Polarizability: 18.423212 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 135 °C(lit.); ca 263°C dec.

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%
• Linear Formula: CH3CONHC6H4B(OH)2

DETAILS

Sigma Aldrich - 566012

Other Notes
Contains varying amounts of anhydride.
Packaging
1 g in glass bottle
Application
Reactant involved in:
• Suzuki-Miyaura coupling reactions1
• Trifluoromethylation2Reactant involved in the synthesis of a variety of inhibitors including:
• NR2B subtype of NMDA receptor antagonists for antidepressant activity3
• Biphenylylmethylimidazole derivatives for use as 17,20-lyase inhibitors4
• (Indolyl)-3,5-substituted benzene analogs with antimitotic and antitumor activity5
• Substituted pyrrolidines and tetrahydrofurans as AMPA receptor positive modulators6