(4-carbamoylphenyl)boronic acid

• ChemBase ID: 10541
• Molecular Formular: C7H8BNO3
• Molecular Mass: 164.95432
• Monoisotopic Mass: 165.05972352
• SMILES: C(=O)(c1ccc(cc1)B(O)O)N
• Canonical SMILES: OB(c1ccc(cc1)C(=O)N)O
• InChI: InChI=1S/C7H8BNO3/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,11-12H,(H2,9,10)
• InChIKey: GNRHNKBJNUVWFZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-carbamoylphenyl)boronic acid
• IUPAC Traditional name: 4-carbamoylphenylboronic acid
• Synonyms: 4-(Aminocarbonyl)benzeneboronic acid; 4-Carbamoylbenzeneboronic acid; Benzamide-4-boronic acid; 4-Carbamoylbenzeneboronic acid; 4-Carbamoylphenylboronic acid; 4-Aminocarbonylphenylboronic acid; 4-AMINOCARBONYLPHENYLBORONIC ACID; 4-Carbamoylphenylboronic acid; 4-甲酰胺基苯硼酸; 4-氨基甲酰基苯硼酸

Database IDs

• CAS Number: 123088-59-5
• MDL Number: MFCD03411940
• PubChem SID: 160973848; 24885784
• PubChem CID: 2737811

CALCULATED PROPERTIES

• Acid pKa: 8.602169
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.29055843
• LogD (pH = 7.4): 0.26459524
• Log P: 0.2909
• Molar Refractivity: 39.6819 cm^3
• Polarizability: 16.390451 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 229-234 °C; 229-234°C°C

Safety Information

• Storage Warning: IRRITANT; Irritant/Store under inert gas/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: 95%; 97%; 98%
• Linear Formula: (H2NCO)C6H4B(OH)2

DETAILS

Sigma Aldrich - 683876

Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Suzuki-Miyaura, Sonogashira and Buchwald-Hartwig cross-coupling reactions for the synthesis of substituted pyrene derivatives1
• Suzuki-Miyaura reactions for the synthesis of aryl-substituted oxabenzindoles and methanobenzindoles2 or 2-aminoimidazole triazoles3
• Three-component coupling with triflates and alkenes4Reactant involved in synthesis of biologically active molecules including:
• Hybrid peptidomimetic molecules as STAT3 protein inhibitors5
• Vasopressin V1B receptor antagonists for use as antidepressants oand anxiolytics6
• (Thienopyridine)caboxamides as CHK1 inhibitors7