(2-nitrophenyl)boronic acid

• ChemBase ID: 74809
• Molecular Formular: C6H6BNO4
• Molecular Mass: 166.92714
• Monoisotopic Mass: 167.03898808
• SMILES: B(c1ccccc1[N+](=O)[O-])(O)O
• Canonical SMILES: [O-][N+](=O)c1ccccc1B(O)O
• InChI: InChI=1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H
• InChIKey: SFUIGUOONHIVLG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-nitrophenyl)boronic acid
• IUPAC Traditional name: 2-nitrophenylboronic acid
• Synonyms: 2-Nitrobenzeneboronic acid; o-Nitrobenzeneboronic acid; 2-Nitrophenylboronic acid; 2-Nitrophenylboronic acid; 2-Nitrobenzeneboronic acid; (2-Nitrophenyl)boronic acid; 2-Nitrophenylboronic acid; 2-硝基苯硼酸

Database IDs

• CAS Number: 5570-19-4; 190788-59-1
• MDL Number: MFCD00161358
• Beilstein Number: 3032097
• PubChem SID: 162039727; 24885182
• PubChem CID: 2773548

CALCULATED PROPERTIES

• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 7.8239956
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5913564
• LogD (pH = 7.4): 1.4550395
• Log P: 1.5934
• Molar Refractivity: 36.924 cm^3
• Polarizability: 15.469442 Å^3
• Polar Surface Area: 83.6 Å^2

PROPERTIES

Physical Property

• Melting Point: 149-151°C; 155-160 °C

Safety Information

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

Product Information

• Purity: 96%; 97%; 98%
• Linear Formula: (O2N)C6H4(B(OH)2)

DETAILS

Sigma Aldrich - 673862

Application
Used in a preparation of unsymmetrical 2,2′-dinitrobiphenyls via Suzuki-Miyaura cross-coupling with nitrophenyl halides.7
Boronic acid catalyst used for:
• Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azides1
• Transposition of allylic alcohols and Meyer-Schuster rearrangements2Reactant involved in:
• Suzuki-Miyaura cross-coupling reactions with aryl halides3 or nitroarenediazonium tetrafluoroborates4
• Copper-catalyzed halogenation5
• Oxidative arylation of aminopyrazolyl disulfides6
Other Notes
May contain varying amounts of anhydride
Packaging
1, 5 g in glass bottle