(3-nitrophenyl)boronic acid

• ChemBase ID: 2511
• Molecular Formular: C6H6BNO4
• Molecular Mass: 166.92714
• Monoisotopic Mass: 167.03898808
• SMILES: OB(O)c1cccc(c1)[N+](=O)[O-]
• Canonical SMILES: OB(c1cccc(c1)[N+](=O)[O-])O
• InChI: InChI=1S/C6H6BNO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,9-10H
• InChIKey: ZNRGSYUVFVNSAW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-nitrophenyl)boronic acid
• IUPAC Traditional name: β-(3-nitrophenyl)-boronic acid; 3-nitrophenylboronic acid
• Synonyms: 3-Nitrobenzeneboronic acid; (3-nitrophenyl)boranediol; 3-Nitrophenylboronic Acid; m-Nitrobenzeneboronic acid; m-Nitrophenylboronic acid; NSC 401539; NSC 59739; 3-Nitrobenzeneboronic acid; 3-Nitrophenylboronic acid; 3-Nitrophenylboronic acid; 3-Nitrophenylboric acid; 3-Nitrobenzeneboronic acid; 间硝基苯硼酸; 3-硝基苯硼酸

Database IDs

• CAS Number: 13331-27-6
• MDL Number: MFCD00007193
• Beilstein Number: 2938638
• PubChem SID: 46507867; 24859487; 160965961
• PubChem CID: 1677

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.387791
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5928411
• LogD (pH = 7.4): 1.5511011
• Log P: 1.5934
• Molar Refractivity: 36.924 cm^3
• Polarizability: 15.466121 Å^3
• Polar Surface Area: 83.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.52
• LOG S: -2.08
• Solubility (Water): 1.40e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 284 - 285°C; 284-285 °C (dec.)(lit.); 288-290°C; 289-291°C; ca 285°C dec.
• Hydrophobicity(logP): 1.338

Safety Information

• Storage Warning: Harmful; Hygroscopic; IRRITANT
• RTECS: CY8980000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: true; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: 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: ≥97%; 95%; 97%; 98%
• Linear Formula: O2NC6H4B(OH)2

DETAILS

DrugBank - DB02797

Drug information: experimental

Sigma Aldrich - 325104

Application
Catalyzes ene carbocyclization of acetylenic dicarbonyl compounds8
Reactant involved in:
• Copper-catalyzed arylation1
• Palladium-catalyzed decarboxylative coupling2
• Suzuki-Miyaura cross-coupling3
• Oxidative carbocyclization / arylation4
• Addition to arylpropargyl alcohols5Additionally used as a reactant for synthesizing biologically active molecules such as:
• Inhibitors of angiogenesis6
• Biaryl-olefins with antiproliferative activities7
Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle

REFERENCES

• Reagent for derivatization of diols and diamines for GC: Chromatographia, 11, 347 (1978).
• Oxidative conversion of arylboronic acids to phenols with potassium monopersulfate in buffered aqueous acetone (in situ dimethyldioxirane) is exemplified for this compound: Tetrahedron Lett., 36, 5117 (1995).
• Mild Lewis acid catayst, for example in the selective transesterification of ?-keto esters: Synlett, 415 (2006). See also 3,4,5-Trifluorobenzeneboronic acid, L18519. For reactions of boronic acids, see Appendix 5.