5172-02-1

Usage

Uses

1. Used in Chemical Synthesis:
1-Chloro-4-(phenylethynyl)benzene is used as a key intermediate in the preparation of various naphthalene derivatives, such as 1-(4-chlorophenyl)-4-methyl-2-phenylnaphthalene and 2-(4-chlorophenyl)-4-methyl-1-phenylnaphthalene. These compounds are synthesized as a 1:1 mixture, which can be further utilized in various applications.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-chloro-4-(phenylethynyl)benzene may be employed as a building block for the development of novel drugs. Its unique structure can be exploited to create new molecules with potential therapeutic properties.
3. Used in Material Science:
1-CHLORO-4-(PHENYLETHYNYL)BENZENE 98 may also find applications in the field of material science, where it can be used to develop new materials with specific properties, such as improved conductivity, strength, or stability.
4. Used in Research and Development:
1-Chloro-4-(phenylethynyl)benzene can be utilized in research and development laboratories for studying the properties of alkynes and their potential applications in various fields, including chemistry, biology, and materials science.

InChI:InChI=1/C14H9Cl/c15-14-10-8-13(9-11-14)7-6-12-4-2-1-3-5-12/h1-5,8-11H

Upstream product

• 1889-71-0 4'-chloro-2-phenylacetophenone 
• 13146-23-1 copper(I) phenylacetylenide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 1199-95-7 1-(trimethylstannyl)-2-phenylethyne 
• 106-48-9 4-chloro-phenol 
• 536-74-3 phenylacetylene 
• 142819-62-3 1-(benzotriazol-1-yl)-1-(p-chlorophenyl)-2-phenylethylene 
• 75354-71-1 1-Chlor-1-phenyl-2-(4-chlorphenyl)-ethylen 
• 106-39-8 bromochlorobenzene 
• 106-46-7 para-dichlorobenzene 
• 201230-82-2 carbon monoxide 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 873-73-4 4-n-chlorophenylacetylene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 14087-87-7 2-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-one 
• 23909-34-4 2-Phenyl-6-chlor-indanon-⁽¹⁾ 
• 22711-23-5 4-chlorobenzil 
• 120106-67-4 4-(4-chlorophenyl)-5-phenyl-1H(2H)-[1,2,3]triazole 
• 6140-44-9 trans-1-(p-Chlor-phenyl)-2-phenyl-1-chlor-2-(p-tolylmercapto)-ethylen 
• 6140-46-1 trans-1-Phenyl-2-(p-chlor-phenyl)-1-chlor-2-(p-tolylmercapto)-ethylen 
• 202479-62-7 ethyl 2-(4-chlorophenyl)-3-phenyl-cycloprop-2-ene-1-carboxylate 
• 910302-30-6 (E)-1-(p-chlorophenyl)-2-phenyl-1-(phenylthio)ethylene 
• 910302-32-8 (E)-1-(p-chlorophenyl)-2-phenyl-2-(phenylthio)ethylene 
• 910302-33-9 (Z)-1-(p-chlorophenyl)-2-phenyl-2-(phenylthio)ethylene 
• 134-85-0 4-chlorobenzophenone 
• 1657-49-4 1-chloro-4-[(Z)-2-phenylethenyl]benzene 
• 120106-67-4 4-(4-chlorophenyl)-5-phenyl-2H-1,2,3-triazole 
• 1185004-38-9 chloro-4-(1,1,2,2-tetrafluoro-2-phenylethyl)benzene 

Relevant academic research and scientific papers

One-pot Sonogashira–Hydroarylation reaction catalyzed by anionic palladium complexes in an aqueous medium

It was found that anionic Pd(II) complexes of type [CA]2[PdCl4] and [CA]2[Pd2Cl6] (CA = imidazolium or pyridinium cation) are effective catalysts for copper-free Sonogashira coupling in an aqueous med

A facile protocol for copper-free palladium-catalyzed Sonogashira coupling in aqueous media

The combination of a readily available palladium catalyst and an eco-friendly basic aqueous solution of room-temperature ionic liquid, choline hydroxide (ChOH), was used in a facile protocol alternative to the Sonogashira coupling reaction, alkynylation of aryl halides in the absence of a copper cocatalyst and an external base. The dual nature of ChOH to act as a base and a green solvent played a crucial role in the catalytic cycle. The coupling reaction progressed efficiently to form a Csp-Csp2 bond under the identified conditions although the reaction outcome depended significantly on the substrates.

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

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.]

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.

Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles

Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a green protic solvent. This environmentally friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the completion of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation was presented, which allows minimization of chemical waste production.

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.

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.

Simple and efficient diaryl alkyne synthesis method

The embodiment of the invention discloses a simple and efficient diaryl alkyne synthesis method. The method comprises the steps of by taking arylmethylbenzotriazole and aromatic aldehyde as raw materials, carrying out addition and double-beta-elimination reaction under the action of bis (trimethylsilyl) amino salt MN (SiMe3) 2 to synthesize diaryl alkyne by a one-pot method. The raw materials and chemical reagents used in the method are easy to obtain, the reaction conditions are mild, the operation is simple, the substrate universality is good, the product yield is high, and the method is a simple and efficient diaryl alkyne synthesis method.

Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents

A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or aryltitanium substrates gave cross-coupling products good yields. This process was simple and easily performed, which provides an efficient method for the synthesis of 1,2-disubstituted acetylenes derivatives.