172512-93-5

Basic information

• Product Name: 4-cyano-trans-beta-styrylboronic acid pinacol ester
• Synonyms: 4-cyano-trans-beta-styrylboronic acid pinacol ester;(E)-4-(2-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile;Benzonitrile, 4-[(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-;-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)
• CAS NO: 172512-93-5
• Molecular Formula: C₁₅H₁₈BNO₂
• Molecular Weight: 273.1352
• Mol File: 172512-93-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 338.5±52.0 °C(Predicted)
• Appearance: /
• Density: 1.05±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-cyano-trans-beta-styrylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-cyano-trans-beta-styrylboronic acid pinacol ester(172512-93-5)
• EPA Substance Registry System: 4-cyano-trans-beta-styrylboronic acid pinacol ester(172512-93-5)

Safety Data

• Hazardous Substances Data: 172512-93-5(Hazardous Substances Data)

Usage

General Description

4-cyano-trans-beta-styrylboronic acid pinacol ester is a chemical compound used in organic synthesis and medicinal chemistry. It is a boronic acid derivative and is often employed as a reagent in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds. 4-cyano-trans-beta-styrylboronic acid pinacol ester is also utilized in the development of new pharmaceuticals and agrochemicals due to its ability to form stable complexes with various functional groups. Additionally, it has shown potential in the treatment of cancer and other diseases, making it a valuable tool in drug discovery and development. However, its toxicity and potential environmental impact should be carefully considered when handling and disposing of this compound.

Upstream product

• 3435-51-6 4-ethenylbenzonitrile 
• 73183-34-3 bis(pinacol)diborane 
• 3032-92-6 4-cyanophenylacetylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 433941-71-0 (E)-4-(3,3,3-trifluoroprop-1-enyl)benzenecarbonitrile 

Relevant articles and documents

Selective hydroboration of alkynes via multisite synergistic catalysis by PCN-222(Cu)

Zirconium-based porphyrinic MOFs (PMOFs, MOF = metal-organic framework) have gained considerable attention in the field of electric/thermo/photo-catalysis as heterogeneous single-site catalysts; however, the study on multisite synergistic catalysis of PMO

Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies

Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.

AgSbF6-Catalyzed: Anti -Markovnikov hydroboration of terminal alkynes

AgSbF6-Catalyzed anti-Markovnikov addition of pinacolborane (HBpin) to terminal alkynes to produce the E-vinylboronates is reported. This efficient methodology is scalable, compatible with sterically and electronically diverse alkynes, and works at room temperature under solvent-free condition. The utility of this method is demonstrated in the facile synthesis of the clinically important (E)-2,4,3′,5′-tetramethoxystilbene.