5216-36-4

Usage

Uses

Used in Organic Synthesis:
4,4'-Dicyanostilbene is used as a building block in organic synthesis for its strong electron-withdrawing nature, which is beneficial in various chemical reactions.
Used in Dye and Optical Brightener Manufacturing:
Leveraging its fluorescent properties, 4,4'-Dicyanostilbene is used as a component in the manufacturing of dyes and optical brighteners, enhancing the color and luminosity of various products.
Used in Sensor Development:
Due to its unique optical and electronic properties, 4,4'-Dicyanostilbene is utilized in the development of sensors, where its responsive characteristics to different stimuli can be harnessed for detecting or measuring various substances.
Used in Organic Light-Emitting Diode (OLED) Technology:
4,4'-Dicyanostilbene is employed in the advancement of OLED technology, where its electronic properties contribute to the efficiency and performance of light-emitting devices.
Used in Advanced Technological Devices:
4,4'-DICYANOSTILBENE's unique properties position it for use in the development of other advanced technological devices that require specific optical and electronic characteristics.

Upstream product

• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 130987-65-4 α,α'-dibromo-bibenzyl-4,4'-dicarbonitrile 
• 623-00-7 4-bromobenzenecarbonitrile 
• 3032-92-6 4-cyanophenylacetylene 
• 104-85-8 para-methylbenzonitrile 
• 4137-78-4 4,α,α,4',α',α'-hexachloro-bibenzyl 
• 3058-39-7 4-iodobenzonitrile 
• 59507-56-1 1,2-bis(methylthio)acetylene 
• 994-71-8 bis(tributylstannyl)acetylene 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 1066-54-2 trimethylsilylacetylene 
• 223562-46-7 4-(prop-1-yn-1-yl)benzonitrile 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 2510-73-8 cis-4,4'-dicyanostilbene 
• 5216-37-5 (E)-4,4'-dicyanostilbene 
• 122-06-5 cis-stilbene-dicarboxamidine-(4.4') 
• 130987-65-4 α,α'-dibromo-bibenzyl-4,4'-dicarbonitrile 
• 1032285-63-4 (2E,4E)-N-tert-butyl-4,5-bis(4-cyanophenyl)penta-2,4-dienamide 
• 1032285-45-2 (2E,4Z)-N-tert-butyl-4,5-bis(4-cyanophenyl)penta-2,4-dienamide 
• 1088706-06-2 (E,E)-1,4-dichloro-1,2,3,4-tetrakis(4-cyanophenyl)buta-1,3-diene 
• 1192648-74-0 5,6-bis(4-cyanophenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one 
• 1208341-99-4 6-(4-cyanophenyl)-7,8-dipropyl-2-naphthonitrile 
• 1259487-37-0 1-benzyl-4,5-bis[4-cyanophenyl]-1H-1,2,3-triazole 
• 1352657-93-2 1-(pentafluorophenyl)-3,4-bis(4-cyanophenyl)isoquinoline 
• 1374337-08-2 C₂₄H₁₈N₂Si 
• 1445990-49-7 5-(4-cyanophenyl)-10-(4-methoxyphenyl)indeno[2,1-a]indene-2-carbonitrile 

Relevant academic research and scientific papers

One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives

The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.

Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations

Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Asymmetric Dearomatization of Indole by Palladium/PC-Phos-Catalyzed Dynamic Kinetic Transformation

A palladium-catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3-arylindoles with internal alkynes was developed with the use of achiral Xantphos and chiral sulfinamide phosphine ligand (PC-Phos) as the co-ligands. This method could deliver various spiro[indene-1,3′-indole] compounds in good yields (up to 95 % yield) with up to 98 % ee. The salient features of the transformation include the use of readily available substrates, ease of scale-up and the versatile functionalization of the products. The mechanistic experiments gave some insights on active intermediates.

"canopy Catalysts" for Alkyne Metathesis: Molybdenum Alkylidyne Complexes with a Tripodal Ligand Framework

A new family of structurally well-defined molybdenum alkylidyne catalysts for alkyne metathesis, which is distinguished by a tripodal trisilanolate ligand architecture, is presented. Complexes of type 1 combine the virtues of previous generations of silanolate-based catalysts with a significantly improved functional group tolerance. They are easy to prepare on scale; the modularity of the ligand synthesis allows the steric and electronic properties to be fine-tuned and hence the application profile of the catalysts to be optimized. This opportunity is manifested in the development of catalyst 1f, which is as reactive as the best ancestors but exhibits an unrivaled scope. The new catalysts work well in the presence of unprotected alcohols and various other protic groups. The chelate effect entails even a certain stability toward water, which marks a big leap forward in metal alkylidyne chemistry in general. At the same time, they tolerate many donor sites, including basic nitrogen and numerous heterocycles. This aspect is substantiated by applications to polyfunctional (natural) products. A combined spectroscopic, crystallographic, and computational study provides insights into structure and electronic character of complexes of type 1. Particularly informative are a density functional theory (DFT)-based chemical shift tensor analysis of the alkylidyne carbon atom and 95Mo NMR spectroscopy; this analytical tool had been rarely used in organometallic chemistry before but turns out to be a sensitive probe that deserves more attention. The data show that the podand ligands render a Mo-alkylidyne a priori more electrophilic than analogous monodentate triarylsilanols; proper ligand tuning, however, allows the Lewis acidity as well as the steric demand about the central atom to be adjusted to the point that excellent performance of the catalyst is ensured.

Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids

Abstract: The reaction of simple alkynoate salts with isolated arenediazonium tetrafluoroborate salts that had been pre-conditioned with the gold(I) catalyst AuCl(Me2S) led to the formation of cross-coupled products via a decarboxylative Sonogashira reaction process in modest yield and under mild conditions. The major by-product is a defunctionalized aryl moiety stemming from the diazonium salt, which competitively forms via hydrodediazonation. Good functional group tolerance and reaction site selectivity were attained in this limited investigation.

Rh(III)-Catalyzed meta-C-H Alkenylation with Alkynes

Rh(III)-catalyzed meta-C-H functionalization reactions are still rare. Herein, we report the first example of Rh(III)-catalyzed meta-C-H alkenylation with disubstituted alkynes directed by a U-shaped nitrile template. Exclusive regio-selectivity has been achieved using unsymmetrical aryl and alkyl-disubstituted alkynes to afford synthetically valuable trisubstituted olefins. Propargyl alcohols are also compatible, affording complex allylic alcohols. Notably, transition metal-catalyzed meta-alkenylation with alkynes has not been successful with Pd catalysts.

Pd-Catalyzed Alkyne Insertion/C-H Activation/[4 + 2] Carboannulation of Alkenes to the Synthesis of Polycyclics

An unprecedented Pd-catalyzed alkyne insertion/C-H activation/intramolecular [4 + 2] carboannulation of alkenes has been reported. In this transformation, the C-H activation was triggered by an in situ generated alkenylpalladium species via the Pd-catalyzed cross-coupling reaction of aryl iodides and alkynes. Subsequently, the resulting five-membered C, C-palladacycle intermediates were added across the alkenes, providing a unique approach to access diversified polycyclics in good efficiency. Two new rings and three C-C bonds were formed in one pot.

Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines

We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.

Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization

Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.