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

• 623-00-7 4-bromobenzenecarbonitrile 
• 536-74-3 phenylacetylene 
• 3058-39-7 4-iodobenzonitrile 
• 1849-25-8 4-phenylethynylphenylamine 
• 123-75-1 pyrrolidine 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 637-44-5 phenylpropyolic acid 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 3032-92-6 4-cyanophenylacetylene 
• 66003-78-9 triphenylsulfonium trifluoromethanesulfonate 
• 100-52-7 benzaldehyde 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 369-57-3 benzenediazonium tetrafluoroborate 

Downstream Products

• 10270-27-6 1-(4-cyanophenyl)-2-phenylethane 
• 1552-58-5 (Z)-4-cyanostilbene 
• 94872-65-8 4-(3-phenylquinoxalin-2-yl)benzonitrile 
• 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 
• 1613435-58-7 5-methyl-3-(4-phenylethynylphenyl)isoquinolin-1(2H)-one 

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.]

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

Palladium-catalyzed decarbonylative sonogashira coupling of terminal alkynes with carboxylic acids

A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.

Copper-mediated conversion of alkynes into nitriles via iodotriazoles

We disclose our studies on a copper-mediated reaction of alkynes with trimethylsilyl azide to afford nitriles, and proposed a reaction mechanism, which involves an iodoalkyne and an iodotriazole as intermediates.

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products

Conversion of the numerous aryl ketones into aryl electrophiles via Ar-C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol in drug discovery and chemical biology are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products. More importantly, two different biologically important fragments derived from a pharmaceutical and natural product could be connected by the consecutive alkynylation of ketones. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynylation.

Xantphos-coordinated palladium dithiolates: Highly efficient catalyst for decarboxylative Sonogashira reaction into corresponding alkynes

This work reports Xantphos-coordinated palladium dithiolate complexes as catalysts for decarboxylative Sonogashira coupling reaction of phenyl propiolic acid and 2-butynoic acid with various iodoarenes. These palladium aryl dithiolate complexes were synthesized and characterized by 1H and 31P nuclear magnetic resonance (NMR) spectroscopy, melting point, and elemental analysis (CHNS). Synthetic utility for the reported protocol is explored for the effect of various functional groups on the yield of corresponding heteroaryl alkynes. The current protocol showed excellent catalytic activity towards decarboxylative alkynylation reaction with high turn-over number (TON) up to 105 and turn-over frequency (TOF) up to 104 h?1. The catalyst could be recycled up to six recycles without losing its catalytic activity. The in situ generation of palladium nanoparticles (PdNPs) was observed after the third recycle, and the amount was significant after the sixth recycle, which were confirmed and characterized by powder X-ray diffraction (XRD), scanning electron microscope (SEM), and energy-dispersive X-ray (EDX) analysis and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of the reaction is attributed to the formation of PdNPs.

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.