(5-amino-2-acetamidophenyl)boronic acid

• ChemBase ID: 158853
• Molecular Formular: C8H11BN2O3
• Molecular Mass: 193.99554
• Monoisotopic Mass: 194.08627262
• SMILES: c1cc(cc(c1NC(=O)C)B(O)O)N
• Canonical SMILES: CC(=O)Nc1ccc(cc1B(O)O)N
• InChI: InChI=1S/C8H11BN2O3/c1-5(12)11-8-3-2-6(10)4-7(8)9(13)14/h2-4,13-14H,10H2,1H3,(H,11,12)
• InChIKey: GZPCXQOFTGPVJZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5-amino-2-acetamidophenyl)boronic acid
• IUPAC Traditional name: 5-amino-2-acetamidophenylboronic acid
• Synonyms: [2-(Acetylamino)-5-aminophenyl]boronic Acid; 2-Acetamido-5-aminophenylboronic Acid

Database IDs

• CAS Number: 136237-84-8
• PubChem SID: 162252988
• PubChem CID: 46738912

CALCULATED PROPERTIES

• Acid pKa: 8.512624
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 0.18054084
• LogD (pH = 7.4): 0.14997333
• Log P: 0.1821
• Molar Refractivity: 50.1669 cm^3
• Polarizability: 19.579128 Å^3
• Polar Surface Area: 95.58 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A139500

o-Acetamidophenylboronic acids may serve as novel agents for bioconjugation reactions involving carbohydrate moieties.

REFERENCES

• Cai, S.X., et al.: Bioconjugate Chem., 2, 317 (1991)