29822-79-5

Usage

Uses

Used in Organic Synthesis:
4-(2-Phenyleth-1-ynyl)benzonitrile is used as a building block in organic synthesis for the creation of more complex molecules, leveraging its unique structure to form new chemical entities.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4-(2-Phenyleth-1-ynyl)benzonitrile serves as a key component in the design and synthesis of novel therapeutic agents, potentially contributing to the development of new drugs.
Used in Pharmaceutical Development:
4-(2-Phenyleth-1-ynyl)benzonitrile is used as a precursor in pharmaceutical development, where its chemical properties may be harnessed to produce compounds with specific medicinal applications.
Used in Materials Science:
Within materials science, 4-(2-Phenyleth-1-ynyl)benzonitrile may be utilized in the development of new materials, taking advantage of its structural attributes to achieve desired material properties.
Used in Chemical Education and Research:
4-(2-Phenyleth-1-ynyl)benzonitrile can be employed as a teaching aid and research tool in academic and research settings, helping to illustrate concepts in organic and medicinal chemistry, as well as in the study of chemical reactions and mechanisms.

InChI:InChI=1/C15H9N/c16-12-15-10-8-14(9-11-15)7-6-13-4-2-1-3-5-13/h1-5,8-11H

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 3058-39-7 4-iodobenzonitrile 
• 1199-95-7 1-(trimethylstannyl)-2-phenylethyne 
• 623-00-7 4-bromobenzenecarbonitrile 
• 536-74-3 phenylacetylene 
• 1122-79-8 potassium phenylacetylide 
• 591-50-4 iodobenzene 
• 3032-92-6 4-cyanophenylacetylene 
• 131356-52-0 2,2-dibromo-1-(4-cyanophenyl)ethene 
• 934-56-5 trimethyl(phenyl)stannane 
• 1849-25-8 4-phenylethynylphenylamine 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 623-03-0 4-Cyanochlorobenzene 
• 62-53-3 aniline 

Downstream Products

• 862604-32-8 CNC₆H₄CSn(C₄H₉)3CHC₆H₅ 
• 862604-33-9 CNC₆H₄CHCSn(C₄H₉)3C₆H₅ 
• 40396-60-9 4-(1,1,2,2-tetrafluoro-2-phenylethyl)benzonitrile 
• 1350432-07-3 2,4-bis-(4-cyanophenyl)-5-phenyl[1,2,3]triazole 
• 1350432-08-4 2-(4-cyanobenzyl)-4-(4-cyanophenyl)-5-phenyl[1,2,3]triazole 
• 25739-23-5 4-(phenylethynyl)benzoic acid 
• 1171122-83-0 methyl 4-(3-phenyl-1H-indol-2-yl)benzoate 
• 93503-74-3 4-(2-phenyl-1H-indol-3-yl)benzoic acid methyl ester 
• 42497-80-3 methyl 4-(phenylethynyl)benzoate 
• 144054-19-3 4-(3-phenyl-1H-indol-2-yl)benzonitrile 
• 833-50-1 2-phenylbenzo[d]oxazole 
• 838-33-5 4-( benzoxazol-2-yl)benzonitrile 
• 57341-98-7 4-(phenylethynyl)benzaldehyde 

Relevant academic research and scientific papers

Microwave-assisted copper-catalyzed Sonogashira reaction in PEG solvent

A catalytic system composed of copper salt, potassium carbonate and appropriate poly(ethylene glycol) (PEG; liquid or solid, various molecular weight: 300 MW 3400) was developed to perform a Sonogashira arylation under microwave activation. In the prese

Palladium nanoclusters in Sonogashira cross-coupling: A true catalytic species?

The question of whether palladium nanoclusters are the actual catalysts in the so-called 'cluster-catalyzed Sonogashira cross-coupling' is investigated, using the coupling of phenylacetylene with 4-bromobenzonitrile as a model reaction. By combining a detailed kinetic analysis with transmission electron microscopy (TEM), we show that a soluble species must be present in the system when Pd nanoclusters are used as catalysts. Various Pd clusters show similar kinetic profiles to that of a homogeneous Pd(dba)2 complex. Most importantly, TEM analysis of samples taken before, during, and after the reaction shows that the cluster size decreases during the reaction. Based on these findings, we present a possible two-path mechanism for Sonogashira cross-coupling reactions in the presence of Pd nanoclusters.

Zeolitic imidazolate frameworks-67 (ZIF-67) supported PdCu nanoparticles for enhanced catalytic activity in Sonogashira-Hagihara and nitro group reduction under mild conditions

A bimetallic PdCu supported on amine functionalized ZIF-67 is shown to be efficient catalyst in Sonogashira-Hagihara coupling reaction of aryl iodides at room temperature and aryl bromides at 40 oC. In addition, the catalyst is used in the reduction of 4-

Introduction of a Recyclable Basic Ionic Solvent with Bis-(NHC) Ligand Property and The Possibility of Immobilization on Magnetite for Ligand- and Base-Free Pd-Catalyzed Heck, Suzuki and Sonogashira Cross-Coupling Reactions in Water

A new versatile and recyclable NHC ligand precursor has been developed with ligand, base, and solvent functionalities for the efficient Pd-catalyzed Heck, Suzuki and Sonogashira cross-coupling reactions under mild conditions. Furthermore, NHC ligand precursor was immobilized on magnetite and its catalytic activity was also evaluated towards the coupling reactions as a heterogeneous catalyst. The NHC ligand precursor was prepared with imidazolium functionalization of TCT followed by a simple ion exchange by hydroxide ions. However, the results revealed an excellent catalytic activity for the both homogeneous and heterogeneous catalytic systems. 1.52?g.cm?3 and 1194 cP was obtained for the density and viscosity of the NHC ligand precursor respectively. On the other hand, the heterogeneous type could be readily recovered from the reaction mixture and reused for several times while preserving its properties. Heterogeneous nature of the magnetic catalyst was studied by hot filtration, mercury poisoning, and three-phase tests. High to excellent yields were obtained for all entries for the both homogeneous and heterogeneous catalysts, which reflects the high consistency of the catalyst. Graphic Abstract: [Figure not available: see fulltext.]

Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent

Cellulose-modified magnetite-graphene oxide nanocomposite was prepared via click reaction and utilized for immobilization of palladium (Pd) nanoparticles without using additional reducing agent. The abundant OH groups of cellulose provided the uniform dispersion and high stability of Pd nanoparticles, while magnetite-graphene oxide as a supporting material offered high specific surface area and easy magnetic separation. The as-prepared nanocomposite served as a heterogeneous catalyst for the Heck and Sonogashira coupling reactions in various hydrophilic and hydrophobic deep eutectic solvents (DESs) as sustainable and environmentally benign reaction media. Among the fifteen DESs evaluated for coupling reactions, the hydrophilic DES composed of dimethyl ammonium chloride and glycerol exhibited the best results. Due to the low miscibility of catalyst and DES in organic solvents, the separated aqueous phase containing both of the catalyst and DES can be readily recovered by evaporating water and retrieved eight times with negligible loss of catalytic performance.

Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction

Inspired by the synthesis of triple-shelled periodic mesoporous organosilica hollow spheres, a straightforward and controllable approach for the preparation of Co3O4 NPs embedded in triple-shelled graphitic carbon nitride has been es

Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation to Achieve Isoquinoline Synthesis

We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.

Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling

Glycosyl triazoles have been introduced as efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect t

Aerobic Cu and amine free Sonogashira and Stille couplings of aryl bromides/chlorides with a magnetically recoverable Fe3O4@SiO2 immobilized Pd(II)-thioether containing NHC

Two value added C–C cross coupling reactions; Sonogashira and Stille couplings were achieved at milder conditions in the catalytic presence of a magnetically recoverable heterogeneous catalyst Fe3O4@SiO2@NHC^SPh-Pd(II). The catalyst was earlier reported for Suzuki-Miyaura reaction, and as an extension of its catalytic efficiency, the Stille and Sonogashira cross coupling reactions under aerobic condition has been explored in present report. The Sonogashira coupling of aryl bromides and terminal alkynes produced an excellent yield (~96% at 0.25 mol% Pd) of the desired coupling product under copper and amines free conditions. Moreover, an excellent Stille coupling of readily available and more latent aryl chlorides and trialkylstannane was obtained (yields up to 95% at 0.25 mol% Pd) in absence of toxic fluorides additives. The broad substrate scope of the catalyst for both the coupling reactions and the magnetically recoverable feature of catalyst make this reaction highly desirable for industrial applications of present heterogeneous catalysis.

Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions

A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.