(4-nitrophenyl)boronic acid

• ChemBase ID: 64737
• Molecular Formular: C6H6BNO4
• Molecular Mass: 166.92714
• Monoisotopic Mass: 167.03898808
• SMILES: [N+](=O)(c1ccc(B(O)O)cc1)[O-]
• Canonical SMILES: OB(c1ccc(cc1)[N+](=O)[O-])O
• InChI: InChI=1S/C6H6BNO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,9-10H
• InChIKey: NSFJAFZHYOAMHL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-nitrophenyl)boronic acid
• IUPAC Traditional name: 4-nitrophenylboronic acid
• Synonyms: 4-Nitrophenylboronic acid; 4-Borononitrobenzene; 4-Nitrobenzeneboronic acid; 4-Nitrobenzeneboronic acid; p-Nitrophenylboronic acid; p-nitro-benzeneboronic acid; 4-Nitrophenylboronic acid; 4-Nitrophenylboronic acid; 4-Nitrobenzeneboronic acid; 4-硝基苯硼酸

Database IDs

• CAS Number: 24067-17-2
• MDL Number: MFCD00161360
• PubChem SID: 24885181; 162030476
• PubChem CID: 2773552

CALCULATED PROPERTIES

• Acid pKa: 8.378958
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5928296
• LogD (pH = 7.4): 1.5502713
• Log P: 1.5934
• Molar Refractivity: 36.924 cm^3
• Polarizability: 15.466752 Å^3
• Polar Surface Area: 83.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 285-290 °C (dec.); 285-290(dec.)°C; ca 285°C dec.

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold/Store under Argon; IRRITANT
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0%; 95%; 95+%; 98%
• Linear Formula: (O2N)C6H4(B(OH)2)

DETAILS

Sigma Aldrich - 673854

Other Notes
May contain varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings1
• Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines2
• Diels-Alder or C-H activation reactions3
• Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulations4
• N-arylation of phenylurea using copper acetylacetonate catalyst5
• Environmentally benign one-pot synthesis through a double arylation process6
• Copper-mediated cyanations7
• copper-catalyzed arylations8
• Regioselective glycosylations9
• Suzuki couplings followed by arylations10
• X-ray absorption on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins11 Reagent used in Preparation of
• Combretastatin analogs as potential antitumor agents12
• Human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses13