4-Cyanophenylboronic Acid
Product Information
Molecular Formula
C7H6NO2B
Molecular Weight
146.94
Description
Reactant involved in: Oxidative hydroxylation; Trifluoromethylation; 1,4-Addition reactions. Precursor in the synthesis of inhibitors such as: Tpl2 kinase inhibitors; P2X7 antagonists used in the treatment of pain. Reagent used for: Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water; Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines with arylboronates; Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids; Ferric perchlorate-promoted reaction of fullerenes with various arylboronic acids to give fullerenyl boronic esters; Phosphine-free Suzuki-Miyaura cross-coupling; Palladacycles as effective catalysts for multicomponent reaction with allylpalladium-intermediates; Chan-Lam-type Cu-catalyzed S-arylation of thiols ; Regioselective cross-coupling reactions under modfied Suzuki and Still cross-coupling reactions with Copper catalysis; Metal-free biaryl coupling in dimethyl carbonate as a solvent. Reagent used for Preparation of: Himbacine analogs as thrombin receptor antagonists and potential antiplatelet agents; Trisulfonated calixarene upper-rim sulfonamido and their complexation with trimethyllysine epigenetic mark; Antimalarial compounds via Suzuki cross-coupling; Deoxyuridine derivatives.
Synonyms
(4-cyanophenyl)boronic acid; (4-cyanophenyl)boronic acid
IUPAC Name
(4-cyanophenyl)boronic acid
SMILES
B(C1=CC=C(C=C1)C#N)(O)O
InChI
InChI=1S/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H
InChI Key
CEBAHYWORUOILU-UHFFFAOYSA-N
Boiling Point
355.9 °C at 760 mmHg
Melting Point
>350 °C (lit.)
Flash Point
Not applicable
Purity
≥ 95 %
Density
1.25 g/cm3
LogP
-0.76192
Safety Information
Precautionary Statement
P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501
Signal Word
Danger
Computed Properties
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
147.0491586 g/mol
Monoisotopic Mass
147.0491586 g/mol
Topological Polar Surface Area
64.2Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
167
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-114016060-A | Synthetic method of phenolic compound | 2021-11-23 |
| CN-113896736-A | Aryl-substituted spirooxazine photochromic compound and preparation method and application thereof | 2021-11-18 |
| CN-114057606-A | Organic luminescent material containing terphenyl, preparation method and application | 2021-11-11 |
| CN-113788790-A | Aromatic heterocyclic amide derivative and application thereof | 2021-10-18 |
| CN-113831292-A | Organic electron transport material containing benzimidazole and anthracene and application thereof | 2021-10-13 |
| CN-113731504-A | Catalyst and preparation method and application thereof | 2021-09-09 |
| CN-113861188-A | Pyrazolo [3,4-b ] pyridine derivative, preparation method thereof and application thereof as HPK1 inhibitor | 2021-08-23 |
| CN-113480475-A | Synthesis method of 4- (2-pyridyl) benzonitrile | 2021-08-20 |
| CN-113512010-A | Photosensitizer with AIE characteristic and capable of overcoming hypoxia, and preparation method and application thereof | 2021-07-20 |
| CN-113527195-A | 5-aryl nicotinamide LSD1/HDAC double-target inhibitor, preparation method and application thereof | 2021-07-07 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22133474 | 2012-01-24 | Boronic acid library for selective, reversible near-infrared fluorescence quenching of surfactant suspended single-walled carbon nanotubes in response to glucose | ACS nano |
| 22065465 | 2011-10-01 | 4-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)benzonitrile | Acta crystallographica. Section E, Structure reports online |
| 21589568 | 2010-11-24 | 4-(1-Naphth-yl)benzonitrile | Acta crystallographica. Section E, Structure reports online |
| 20669927 | 2010-11-11 | Medicinal chemistry as a conduit for the modulation of quorum sensing | Journal of medicinal chemistry |
| 20594849 | 2010-08-01 | Aryl boronic acid inhibition of synthetic melanin polymerization | Bioorganic & medicinal chemistry letters |
| 18983140 | 2008-11-27 | Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase | Journal of medicinal chemistry |
| 17976993 | 2008-01-15 | Synthesis and antiprotozoal activity of novel bis-benzamidino imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines | Bioorganic & medicinal chemistry |
| 16099661 | 2005-12-15 | Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents | Bioorganic & medicinal chemistry |
| 15214792 | 2004-07-01 | Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents | Journal of medicinal chemistry |
| 14561095 | 2003-10-23 | Synthesis and antiprotozoal activity of aza-analogues of furamidine | Journal of medicinal chemistry |
