3-{[4-(dihydroxyboranyl)phenyl]carbamoyl}propanoic acid

• ChemBase ID: 75163
• Molecular Formular: C10H12BNO5
• Molecular Mass: 237.01698
• Monoisotopic Mass: 237.08085289
• SMILES: B(c1ccc(cc1)NC(=O)CCC(=O)O)(O)O
• Canonical SMILES: O=C(Nc1ccc(cc1)B(O)O)CCC(=O)O
• InChI: InChI=1S/C10H12BNO5/c13-9(5-6-10(14)15)12-8-3-1-7(2-4-8)11(16)17/h1-4,16-17H,5-6H2,(H,12,13)(H,14,15)
• InChIKey: VYUCUZOJUHAJLU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[4-(dihydroxyboranyl)phenyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[4-(dihydroxyboranyl)phenyl]carbamoyl}propanoic acid
• Synonyms: N-(4-Phenylboronic)succinamic acid; 4-[(3-Carboxypropanoyl)amino]benzeneboronic acid; N-(4-Phenylboronic)succinamic acid; N-(4-硼苯)琥珀酰胺酸

Database IDs

• CAS Number: 480424-95-1
• MDL Number: MFCD03789260
• PubChem SID: 162040081; 24880948
• PubChem CID: 2769393

CALCULATED PROPERTIES

• Acid pKa: 3.709558
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.0348955
• LogD (pH = 7.4): -2.6454039
• Log P: 0.7572
• Molar Refractivity: 56.3598 cm^3
• Polarizability: 22.693148 Å^3
• Polar Surface Area: 106.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 165-169 °C(lit.)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Linear Formula: (OH)2BC6H4NHCOCH2CH2CO2H

DETAILS

Sigma Aldrich - 578754

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Construction of combinatorial artificial receptor array (CARA)1
• Preparation of hydroxycoumarins and pyranocoumarins via Pechmann condensation and Pd-catalyzed Suzuki coupling as antitumor agents2