4-Cyanophenylboronic acid（contains varying amounts of anhydride） - ≥97% , CAS No.126747-14-6

CAS: 126747-14-6 Cat. No.: C106584 Molecular Weight: 146.94 EC Number: 671-676-8

GRADE & PURITY ≥97%

Synonyms

4-cyanobenzene boronic acid | B-(4-cyanophenyl)-boronic acid | 4-cyanophenyl-boronic acid | AKOS004116072 | (4-cyanophenyl) boronic acid | BCP12932 | J-515232 | BBL101374 | 4-Cyanobenzeneboronic Acid | para-cyanophenylboronic acid | SCHEMBL6016 | Z9153806

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

4-Cyanophenylboronic acid can be used as a reactant in:
Palladium-catalyzed 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 reaction in the presence of dimethyl carbonate as a solvent.
Suzuki-type cross-coupling reaction with pentavalent triarylantimony diacetates in the absence of a base.
It can also be used to prepare:
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.
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

Specifications

Synonyms

4-cyanobenzene boronic acid | B-(4-cyanophenyl)-boronic acid | 4-cyanophenyl-boronic acid | AKOS004116072 | (4-cyanophenyl) boronic acid | BCP12932 | J-515232 | BBL101374 | 4-Cyanobenzeneboronic Acid | para-cyanophenylboronic acid | SCHEMBL6016 | Z9153806

Specifications & Purity

≥97%

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504761107
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504761107
• Canonical Smiles: B(C1=CC=C(C=C1)C#N)(O)O
• IUPAC Name: (4-cyanophenyl)boronic acid
• InChIKey: CEBAHYWORUOILU-UHFFFAOYSA-N
• INCHI: 1S/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H
• Isomeric SMILES: B(C1=CC=C(C=C1)C#N)(O)O
• WGK Germany: 3
• UN Number: 2811
• Molecular Weight: 146.94
• Reaxy-Rn: 6593772
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6593772&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzonitriles

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzonitriles
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzonitriles
• Alternative Parents: Boronic acids Organic metalloid salts Nitriles Organopnictogen compounds Organoboron compounds Organic oxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzonitrile - Boronic acid - Boronic acid derivative - Organic metalloid salt - Nitrile - Carbonitrile - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organic salt - Organonitrogen compound - Organoboron compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MGLL Tchem Monoglyceride lipase (1909 Activities)

Discover Target: MGLL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ENPP2 Tchem Autotaxin (2645 Activities)

Discover Target: ENPP2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Faah Anandamide amidohydrolase (3907 Activities)

Discover Target: Faah

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in Methanol
• Melt Point(°C): >350°C
• Molecular Weight: 146.940 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 147.049 Da
• Monoisotopic Mass: 147.049 Da
• Topological Polar Surface Area: 64.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 167.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

References

1. Shufang Liu, Ziqian Liu, Qing Su, Qiaolin Wu.  (2022)  Multifunctional covalent organic frameworks for photocatalytic oxidative hydroxylation of arylboronic acids and fluorescence sensing for Cu2+.  MICROPOROUS AND MESOPOROUS MATERIALS,      [PMID:] [10.1016/j.micromeso.2022.111737]

2. Jianwen Tian, Muzhou Teng, Mu Song, Zhijia Li, Xiaoyong Zhang, Youqin Xu.  (2021)  A feasible molecular engineering for bright Π-conjugation free radical photosensitizers with aggregation-induced emission.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2021.109651]

3. Tao Ma, Feng Liang.  (2020)  Au–Pd Nanostars with Low Pd Content: Controllable Preparation and Remarkable Performance in Catalysis.  Journal of Physical Chemistry C,      [PMID:] [10.1021/acs.jpcc.0c00031]