521418

4-Cyanophenylboronic acid

≥95%

• Synonym(s): (p-Cyanophenyl)boronic acid, 4-Cyanobenzeneboronic acid, 4-Cyanophenylboric acid
• Linear Formula: NCC₆H₄B(OH)₂
• CAS Number: 126747-14-6
• Molecular Weight: 146.94
• MDL number: MFCD01318968
• UNSPSC Code: 12352103
• PubChem Substance ID: 24874205
• NACRES: NA.22

Properties

• Assay: ≥95%
• mp: >350 °C (lit.)
• SMILES string: OB(O)c1ccc(cc1)C#N
• InChI: 1S/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H
• InChI key: CEBAHYWORUOILU-UHFFFAOYSA-N

Description

Application

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

Other Notes

Contains varying amounts of anhydride

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves