(3-carbamoylphenyl)boronic acid

• ChemBase ID: 10542
• Molecular Formular: C7H8BNO3
• Molecular Mass: 164.95432
• Monoisotopic Mass: 165.05972352
• SMILES: C(=O)(c1cccc(c1)B(O)O)N
• Canonical SMILES: OB(c1cccc(c1)C(=O)N)O
• InChI: InChI=1S/C7H8BNO3/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,11-12H,(H2,9,10)
• InChIKey: WDGWHKRJEBENCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-carbamoylphenyl)boronic acid
• IUPAC Traditional name: 3-carbamoylphenylboronic acid
• Synonyms: 3-(Aminocarbonyl)benzeneboronic acid; 3-Carbamoylbenzeneboronic acid 98%; (3-Carbamoylphenyl)boronic acid; 3-AMINOCARBONYLPHENYLBORONIC ACID; 3-Carbamoylphenylboronic acid; 3-Aminocarbonylphenylboronic acid; Benzamide-3-boronic acid; 3-甲酰胺基苯硼酸; 3-氨基甲酰基苯硼酸

Database IDs

• CAS Number: 351422-73-6
• MDL Number: MFCD03411948
• PubChem SID: 160973849
• PubChem CID: 2737814

CALCULATED PROPERTIES

• Acid pKa: 8.610443
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.29056466
• LogD (pH = 7.4): 0.2650777
• Log P: 0.2909
• Molar Refractivity: 39.6819 cm^3
• Polarizability: 16.389675 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 221-226 °C; 232-238°C

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Linear Formula: (H2NCO)C6H4B(OH)2

DETAILS

Sigma Aldrich - 683868

Packaging
1, 5 g in glass bottle
Application
Reactant involved in the synthesis of a variety of inhibitors including:
• Orally active phosphodiesterase 10A inhibitors1
• Pyrimidine derivatives as TpI2 kinase inhibitors2
• Peptidomimetic inhibitors of STAT3 protein3Reactant involved in:
• Oxidative cross-coupling with mercaptoacetylenes4
• Trifluoromethylation via a Collidine trifluoromethylating agent5
• Suzuki cross-coupling reactions6