(4-cyanophenyl)boronic acid

• ChemBase ID: 7928
• Molecular Formular: C7H6BNO2
• Molecular Mass: 146.93904
• Monoisotopic Mass: 147.04915884
• SMILES: c1c(ccc(c1)B(O)O)C#N
• Canonical SMILES: N#Cc1ccc(cc1)B(O)O
• InChI: InChI=1S/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H
• InChIKey: CEBAHYWORUOILU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-cyanophenyl)boronic acid
• IUPAC Traditional name: 4-cyanophenylboronic acid
• Synonyms: 4-(dihydroxyboranyl)benzonitrile; (4-cyanophenyl)boronic acid; 4-Cyanophenylboronic acid; 4-Cyanobenzeneboronic acid; (p-Cyanophenyl)boronic acid; 4-Cyanobenzeneboronic acid; 4-Cyanophenylboric acid; 4-Cyanophenylboronic acid; 4-Boronobenzonitrile; 4-Cyanobenzeneboronic acid; 4-Cyanophenylboronic acid; 4-氰基苯硼酸

Database IDs

• CAS Number: 126747-14-6
• MDL Number: MFCD01318968
• Beilstein Number: 6593772
• PubChem SID: 24874205; 160971235
• PubChem CID: 2734326

CALCULATED PROPERTIES

• Acid pKa: 8.655867
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.4544984
• LogD (pH = 7.4): 1.4314744
• Log P: 1.4548
• Molar Refractivity: 36.3251 cm^3
• Polarizability: 15.363086 Å^3
• Polar Surface Area: 64.25 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300°C; >350 °C(lit.); >350°C; 300 - 302°C
• Hydrophobicity(logP): 1.028

Safety Information

• Storage Warning: Irritant; KEEP COLD
• European Hazard Symbols: X
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 97%; 98%
• Linear Formula: NCC6H4B(OH)2

DETAILS

Sigma Aldrich - 521418

Other Notes
Contains varying amounts of anhydride
Packaging
1 g in glass bottle
10 g in poly bottle
Application
Reactant involved in:
• Oxidative hydroxylation1
• Trifluoromethylation2
• 1,4-Addition reactions3Precursor in the synthesis of inhibitors such as:
• Tpl2 kinase inhibitors4
• P2X7 antagonists used in the treatment of pain5
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 solventReagent 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