765916-91-4

Basic information

• Product Name: 2-Cyano-3-fluorophenylboronic acid pinacol ester
• Synonyms: 2-Fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;2-Cyano-3-fluorophenylboronic acid pinacol ester;Benzonitrile, 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• CAS NO: 765916-91-4
• Molecular Formula: C₁₃H₁₅BFNO₂
• Molecular Weight: 247.07
• Product Categories: Aryl;Organoborons
• Mol File: 765916-91-4.mol

Chemical Properties

• Boiling Point: 357.8±32.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Cyano-3-fluorophenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyano-3-fluorophenylboronic acid pinacol ester(765916-91-4)
• EPA Substance Registry System: 2-Cyano-3-fluorophenylboronic acid pinacol ester(765916-91-4)

Safety Data

• Hazardous Substances Data: 765916-91-4(Hazardous Substances Data)

Usage

Uses

2-Fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is used as a reagent in the synthesis of tetramethylpiperidinyl benzamides as inhibitors of Enhancer of Zeste Homolog 2 (EZH2).

Upstream product

• 79544-27-7 2-bromo-6-fluorobenzonitrile 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1377997-44-8 2-(2-chloro-4-((2,2,6,6-tetramethylpiperidin-4-yl)methoxy)phenoxy)-6-(pyrimidin-4-yl)benzonitrile 
• 1439559-83-7 2-(2-chloro-4-((1-oxy-2,2,6,6-tetramethylpiperidin-4-yl)methoxy)phenoxy)-6-(pyrimidin-4-yl)benzonitrile 
• 1378005-02-7 2-fluoro-6-(pyrimidin-4-yl)benzonitrile 
• 1332453-13-0 4'-({4-[4-(cyclopropylcarbonyl)piperidin-1-yl]-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl}carbonyl)-3-fluorobiphenyl-2-carbonitrile 
• 765916-92-5 3,2'-difluoro-5'-[3-(2,4-difluorophenyl)-[1,2,4]triazin-5-yl]biphenyl-2-carbonitrile 

Relevant articles and documents

Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation

A new click bioorthogonal reaction system was devised to enable the fast ligation (kON≈340 m-1 s-1) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2-methyl-5-carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration in water, providing submicromolar equilibrium constant (Keq≈105-106 m-1). Efficient protein conjugation under physiological conditions was demonstrated with model proteins thioredoxin and albumin, and characterized by mass spectrometry and gel electrophoresis.

Discovery and optimization of tetramethylpiperidinyl benzamides as inhibitors of EZH2

The identification and development of a novel series of small molecule Enhancer of Zeste Homologue 2 (EZH2) inhibitors is described. A concise and modular synthesis enabled the rapid development of structure-activity relationships, which led to the identification of 44 as a potent, SAM-competitive inhibitor of EZH2 that dose-dependently decreased global H3K27me3 in KARPAS-422 lymphoma cells.