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
Canonical 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
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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