2-Nitrophenylboronic Acid
Product Information
Molecular Formula
C6H6NO4B
Molecular Weight
166.93
Description
Boronic acid catalyst used for: Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azides; Transposition of allylic alcohols and Meyer-Schuster rearrangements. Reactant involved in: Suzuki-Miyaura cross-coupling reactions with aryl halides or nitroarenediazonium tetrafluoroborates; Copper-catalyzed halogenation; Oxidative arylation of aminopyrazolyl disulfides. Used in a preparation of unsymmetrical 2,2'-dinitrobiphenyls via Suzuki-Miyaura cross-coupling with nitrophenyl halides.
Synonyms
(2-nitrophenyl)boronic acid; (2-nitrophenyl)boronic acid
IUPAC Name
(2-nitrophenyl)boronic acid
SMILES
B(C1=CC=CC=C1[N+](=O)[O-])(O)O
InChI
InChI=1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H
InChI Key
SFUIGUOONHIVLG-UHFFFAOYSA-N
Boiling Point
374.8 °C at 760 mmHg
Melting Point
155-160 °C
Flash Point
Not applicable
Purity
99 %
Density
1.40 ± 0.1 g/mL (predicted)
Appearance
White powder
LogP
-0.20220
Safety Information
Hazards
H302 - H315 - H319 - H335
Precautionary Statement
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning
Computed Properties
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Exact Mass
167.0389878 g/mol
Monoisotopic Mass
167.0389878 g/mol
Topological Polar Surface Area
86.3Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
169
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-113980026-A | Carbazole derivative amine compound and organic electroluminescent device comprising same | 2021-11-25 |
| CN-114016060-A | Synthetic method of phenolic compound | 2021-11-23 |
| CN-114057616-A | Method for synthesizing N-substituted benzene sulfonamide compound | 2021-11-12 |
| CN-113929591-A | Inhibitors with antiproliferative activity | 2021-10-09 |
| CN-113717181-A | Host material, organic photoelectric device and display or lighting device | 2021-09-27 |
| CN-113817462-A | Host material, organic photoelectric device and display or lighting device | 2021-09-27 |
| CN-113636975-A | Boscalid hapten, preparation method thereof, antigen, antibody and application thereof | 2021-08-12 |
| CN-113321659-A | Organic electroluminescent material and device thereof | 2021-05-27 |
| CN-113173879-A | Preparation method of seven-element fused ring compound | 2021-04-30 |
| CN-113121584-A | Heterocyclic compound and organic electroluminescent device comprising same | 2021-03-30 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 21967291 | 2011-11-09 | Nitrophenylboronic acids as highly chemoselective probes to detect hydrogen peroxide in foods and agricultural products | Journal of agricultural and food chemistry |
| 20373314 | 2010-05-10 | Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids | Chemistry (Weinheim an der Bergstrasse, Germany) |
| 16935036 | 2006-12-05 | Performances of a multidimensional on-line SPE-LC-ECD method for the determination of three major catecholamines in native human urine: validation, risk and uncertainty assessments | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences |
| 17152980 | 2006-11-01 | [Thieno[3,4-c]quinoline-4-yl-amines--synthesis and investigation of activity against malaria] | Die Pharmazie |
| 16649537 | 2006-04-01 | [Thieno[3,2-c]quinoline-4-yl-amines--synthesis and investigation of activity against malaria] | Die Pharmazie |
| 14684290 | 2004-01-05 | 3-Methoxycarbonyl-5-nitrophenyl boronic acid: high affinity diol recognition at neutral pH | Bioorganic & medicinal chemistry letters |
