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

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

Uses

Used in Organic Synthesis:
4-cyano-trans-beta-styrylboronic acid pinacol ester is used as a reagent in Suzuki-Miyaura cross-coupling reactions for the formation of carbon-carbon bonds. This application is crucial in the synthesis of complex organic molecules and contributes to the advancement of chemical research.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-cyano-trans-beta-styrylboronic acid pinacol ester is utilized in the development of new pharmaceuticals. Its ability to form stable complexes with different functional groups allows for the creation of novel drug candidates with potential therapeutic applications.
Used in Agrochemical Development:
4-cyano-trans-beta-styrylboronic acid pinacol ester is also employed in the development of new agrochemicals, where its reactivity and complex-forming capabilities can lead to the discovery of innovative compounds for agricultural applications.
Used in Drug Discovery and Development:
4-cyano-trans-beta-styrylboronic acid pinacol ester has shown potential in the treatment of cancer and other diseases, making it a valuable tool in drug discovery and development. Its unique properties enable the exploration of new therapeutic avenues and the design of targeted drug molecules.
Used in Cancer Treatment Research:
4-cyano-trans-beta-styrylboronic acid pinacol ester is being investigated for its potential role in cancer treatment. Its ability to form stable complexes with various functional groups may contribute to the development of targeted therapies for specific types of cancer.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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

Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions

The hydroboration of alkynes is crucial due to the wide applications in organic synthesis, while such reaction is often completed with low turnover frequency (TOF) value and long reaction time. Therefore, it is very important and necessary that the hydrob

Reaction Pathways and Redox States in α-Selective Cobalt-Catalyzed Hydroborations of Alkynes

Cobalt(II) alkyl complexes supported by a monoanionic NNN pincer ligand are pre-catalysts for the regioselective hydroboration of terminal alkynes, yielding the Markovnikov products with α:β-(E) ratios of up to 97:3. A cobalt(II) hydride and a cobalt(II) vinyl complex appear to determine the main reaction pathway. In a background reaction the highly reactive hydrido species specifically converts to a coordinatively unsaturated cobalt(I) complex which was found to re-enter the main catalytic cycle.

Direct Synthesis of Alkenylboronates from Alkenes and Pinacol Diboron via Copper Catalysis

We report an efficient approach for the direct synthesis of alkenylboronates using copper catalysis. The Cu/TEMPO catalyst system (where TEMPO = (2,2,6,6-tetramethylpiperidin-1-yl)oxyl) exhibits both excellent reactivity and selectivity for the synthesis of alkenylboronates, starting from inexpensive and abundant alkenes and pinacol diboron. This approach allows for the direct functionalization of both aromatic and aliphatic terminal alkenes. Mechanistic experiments suggest that the alkenylboronates arise from oxyboration intermediates.

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.

Lewis acid catalysis: Regioselective hydroboration of alkynes and alkenes promoted by scandium triflate

The first commercially available scandium-catalysed selective hydroboration of alkynes and alkenes with HBpin (pin = OC-Me2CMe2O) in the presence of a catalytic amount of NaHBEt3 has been developed. This protocol can be applicable to a wide range of substrates including aromatic, aliphatic with cyclic and acyclic side chains, and heteroaryl systems with broad functional-group compatibility. Mechanistic studies revealed that the reaction occurs in a syn fashion via the σ-bond metathesis between the alkenyl scandium species and HBpin.

Transition-metal-free PhI(OAc)2-promoted highly selective hydroboration of terminal alkynes under air

A new transition-metal-free PhI(OAc)2-promoted hydroboration reaction of terminal alkynes with bis(pinacolato)diboron has been developed at room temperature under air. A series of vinyl boronates could be conveniently and efficiently obtained i

N-B dative bond-induced [3.3.0] bicyclic boronate-tethered exo-selective intramolecular Diels-Alder reaction

We report herein a highly exo-selective intramolecular Diels-Alder reaction of alkenyl boronates which employs an N-B dative bond-involved bicyclic rigid tether. Complex C(sp3)-rich polycyclic molecules containing up to 8 stereocenters can be readily formed via an operationally simple two-step procedure.

Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis

A facile synthesis of trifluoromethylated alkenes by the radical-mediated trifluoromethylation of vinyltrifluoroborates has been developed. Togni's reagent serves as a CF3 radical precursor in the presence of the photoredox catalyst [Ru(bpy)3](PF6)2 under visible light irradiation. This new photocatalytic protocol can be applicable to a wide variety of vinylborates containing electronically diverse substituents and hetero-aromatics. The Royal Society of Chemistry 2013.