[4-(dimethylcarbamoyl)phenyl]boronic acid

• ChemBase ID: 64307
• Molecular Formular: C9H12BNO3
• Molecular Mass: 193.00748
• Monoisotopic Mass: 193.09102365
• SMILES: C(=O)(c1ccc(B(O)O)cc1)N(C)C
• Canonical SMILES: OB(c1ccc(cc1)C(=O)N(C)C)O
• InChI: InChI=1S/C9H12BNO3/c1-11(2)9(12)7-3-5-8(6-4-7)10(13)14/h3-6,13-14H,1-2H3
• InChIKey: QJYYVSIRDJVQJW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(dimethylcarbamoyl)phenyl]boronic acid
• IUPAC Traditional name: 4-(dimethylcarbamoyl)phenylboronic acid
• Synonyms: 4-[(Dimethylamino)carbonyl]benzeneboronic acid; 4-Borono-N,N-dimethylbenzamide; 4-(Dimethylcarbamoyl)benzeneboronic acid 97%; 4-(N,N-Dimethylaminocarbonyl)phenylboronic acid; (4-(Dimethylaminocarbonyl)phenyl)boronic acid; 4-(Dimethylcarbamoyl)benzeneboronic acid; 4-Dimethylcarbamoylphenylboronic acid; [4-(N,N-Dimethylaminocarbonyl)phenyl]boronic acid; [4-(N,N-Dimethylcarbamoyl)phenyl]boronic acid; 4-(N,N-Dimethylaminocarbonyl)phenylboronic acid; 4-(Dimethylcarbamoyl)phenylboronic acid; 4-(N,N-二甲基甲酰氨)苯基硼酸; 4-(N,N-二甲氨基甲酰基)苯硼酸

Database IDs

• CAS Number: 405520-68-5
• MDL Number: MFCD02258943
• PubChem SID: 162030046
• PubChem CID: 3503767

CALCULATED PROPERTIES

• Acid pKa: 8.595699
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.78355354
• LogD (pH = 7.4): 0.7572123
• Log P: 0.7839
• Molar Refractivity: 49.4753 cm^3
• Polarizability: 20.058111 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 130-136°C; 141-145 °C

Safety Information

• Storage Warning: IRRITANT; Irritant/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37/39
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥94%; 97%; 98%
• Empirical Formula (Hill Notation): C9H12BNO3

DETAILS

Sigma Aldrich - 715492

General description
May contain varying amounts of anhydride
Packaging
1 g in glass bottle
Application
Reactant for preparation of:
• Selective glucocorticoid receptor agonists1
• (thienopyridine)carboxamides as checkpoint 1 kinase (CHK1) inhibitors2
• [(pyrrolo[2,3-b]pyridinyl)methylene]hydroxybenzofuranones as ATP-competitive inhibitors of the mammalian target of rapamycin3
• Pyrrolopyridines as inhibitors of insulin-like growth factor-1 receptor tyrosine kinase4Reactant for:
• Copper-mediated N-arylation of quinazolinediones5