(2-acetamidophenyl)boronic acid

• ChemBase ID: 34763
• Molecular Formular: C8H10BNO3
• Molecular Mass: 178.9809
• Monoisotopic Mass: 179.07537359
• SMILES: c1(B(O)O)c(NC(=O)C)cccc1
• Canonical SMILES: CC(=O)Nc1ccccc1B(O)O
• InChI: InChI=1S/C8H10BNO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5,12-13H,1H3,(H,10,11)
• InChIKey: UMOPBIVXPOETPG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-acetamidophenyl)boronic acid
• IUPAC Traditional name: 2-acetamidophenylboronic acid
• Synonyms: (2-Acetamidophenyl)boronic acid; 2-Acetamidobenzeneboronic acid; (2-Acetylaminophenyl)boronic acid; 2-Carbamoylbenzeneboronic acid; 2-Acetamidophenylboronic acid; 2-Acetylaminophenylboronic acid; 2-Acetamidobenzeneboronic acid; 2-ACETAMIDOPHENYLBORONIC ACID; 2-乙酰基氨基苯基硼酸; 2-乙酰胺基苯硼酸; 2-乙酰氨基苯硼酸

Database IDs

• CAS Number: 169760-16-1
• MDL Number: MFCD02179474
• PubChem SID: 160998070; 24885788
• PubChem CID: 2737789

CALCULATED PROPERTIES

• Acid pKa: 8.495245
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.96486354
• LogD (pH = 7.4): 0.9319267
• Log P: 0.9653
• Molar Refractivity: 45.4665 cm^3
• Polarizability: 18.42465 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C; >300°C; 300°C

Safety Information

• Storage Warning: Harmful; 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; 96%; 98%
• Linear Formula: (CH3CONH)C6H4B(OH)2

DETAILS

Sigma Aldrich - 683906

General description
May contain varying amounts of anhydride.
Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Reactant for preparation of:
• Highly substituted acenes via rhodium-catalyzed oxidative coupling with alkynes1
• Anticancer pyrimidines with multiple-kinase inhibitory effect2
• 3,4-ring fused 7-azaindoles and deazapurines as potent JAK2 inhibitors3
• Polycyclic azaindoles as JAK2 inhibitors4
• ROS1 receptor tyrosine kinase inhibitors5
• 2-aminopyrazolopyridines as Polo-like kinase 1 inhibitors6