171258-08-5

Usage

Uses

Used in Organic Synthesis:
1-(2-(phenylethynyl)phenyl)ethanone is used as a building block in organic synthesis for the preparation of various organic compounds. Its unique structure allows it to be a versatile component in the creation of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1-(2-(phenylethynyl)phenyl)ethanone is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its properties make it suitable for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
1-(2-(phenylethynyl)phenyl)ethanone also finds application in the agrochemical sector, where it is used in the production of pesticides and other agrochemicals. Its role in these products is crucial for enhancing crop protection and yield.
Used in Dye Production:
1-(2-(phenylethynyl)phenyl)ethanone is employed in the dye industry for the synthesis of various dyes. Its chemical structure contributes to the color and stability of the dyes produced.
Used in Coordination Chemistry:
Additionally, 1-(2-(phenylethynyl)phenyl)ethanone serves as a ligand in coordination chemistry. Its interaction with metal ions allows for the formation of coordination compounds with specific properties, which are useful in various chemical and material science applications.

Upstream product

• 2142-69-0 2-bromophenyl methyl ketone 
• 536-74-3 phenylacetylene 
• 118-93-4 o-hydroxyacetophenone 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 2142-70-3 2-iodoacetophenone 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 637-44-5 phenylpropyolic acid 
• 59046-72-9 o-(phenylethynyl)benzaldehyde 
• 109-89-7 diethylamine 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 129849-05-4 trifluoromethanesulfonic acid 2-acetylphenyl ester 
• 6630-33-7 ortho-bromobenzaldehyde 
• 551-93-9 2-aminoacetophenone 
• 4636-16-2 iodoacetophenone 

Downstream Products

• 192935-79-8 2-(2-Phenylethynyl-phenyl)-oct-3-yn-2-ol 
• 862604-42-0 CH₃C(O)C₆H₄CSn(C₄H₉)3CHC₆H₅ 
• 1263056-82-1 1-(2-(2-(1-cyclopropylideneethyl)phenyl)ethynyl)benzene 
• 1263056-87-6 1,2-dihydro-8-methyl-3-phenylcyclopenta[a]indene 
• 1284293-83-9 C₁₆H₁₂O 
• 1309688-89-8 C₁₆H₁₃N 
• 1309688-79-6 C₂₃H₁₂F₅NO₂ 
• 1310569-56-2 1-(2-acetylphenyl)-2-phenylethane-1,2-dione 
• 1338235-58-7 (E)-3-(6-bromobenzo[d][1,3]dioxol-5-yl)-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one 
• 1338235-52-1 (E)-1-(2-(phenylethynyl)phenyl)-3-(p-tolyl)prop-2-en-1-one 
• 1338235-53-2 (E)-3-(4-chlorophenyl)-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one 
• 1338235-55-4 (E)-3-(2-chlorophenyl)-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one 
• 1338235-54-3 (E)-3-(4-nitrophenyl)-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one 
• 1338235-59-8 (2E,4E)-5-phenyl-1-(2-(phenylethynyl)phenyl)penta-2,4-dien-1-one 

Relevant academic research and scientific papers

Superparamagnetic nanoparticles-supported phosphine-free palladium catalyst for the Sonogashira coupling reaction

Superparamagnetic nanoparticles were synthesized following a microemulsion method, and functionalized with Schiff-base groups on the surface to form immobilized bidentate ligands. The functionalized nanoparticles were complexed with palladium acetate, aff

Concise synthesis of 1,2-dihydroisoquinolines and 1H-isochromenes by carbophilic lewis acid-catalyzed tandem nucleophilic addition and cyclization of 2-(1-alkynyl)arylaldimines and 2-(1-alkynyl)arylaldehydes

(Chemical Equation Presented) By using carbophilic Lewis acids, In(OTf)3, NiCl2, and AuCl(PPh3)/AgNTf 2, a concise and efficient synthesis of 1,3-disubstituted 1,2-dihydroisoquinolines has been achieved via tandem nucleophilic addition and cyclization of 2-(1-alkynyl)arylaldimines. Addition of proton sources such as water, CF3CH2OH, and 2,6-di-tert-butyl-4-methoxyphenol was essential for the Lewis acid-catalyzed tandem reactions with organometallic reagents. By switching these catalysts, various types of nucleophiles such as allylstannanes, silyl enol ethers, alkenylboronic acids, and active methylene compounds could be introduced at the C1 position of 1,2-dihydroisoquinolines in this transformation. Furthermore, this method proved to be applicable to the synthesis of 1H-isochromene derivatives via the same tandem reaction of 2-(1-alkynyl)-arylaldehydes.

Single Cu(I)-Photosensitizer Enabling Combination of Energy-Transfer and Photoredox Catalysis for the Synthesis of Benzo[ b]fluorenols from 1,6-Enynes

An efficient, mild, and atom-economical synthesis of benzo[b]fluorenols from 1,6-enynes has been developed under photocatalytic conditions. A single P/N heteroleptic Cu(I)-photosensitizer might exhibit both energy-transfer and photoredox catalytic activities in the formation of benzo[b]fluorenols.

Mechanistic Investigation of the Formation of Isoindole N-Oxides in the Electron Transfer-Mediated Oxidative Cyclization of 2′-Alkynylacetophenone Oximes

This paper describes a joint experiment-theory investigation of the formation and cyclization of 2′-alkynylacetophenone oxime radical cations using photoinduced electron transfer (PET) with DCA as the photosensitizer. Using a combination of experimental 1H and 13C nuclear magnetic resonance (NMR) spectra, high-resolution mass spectrometry, and calculated NMR chemical shifts, we identified the products to be isoindole N-oxides. The reaction was found to be stereoselective; only one of the two possible stereoisomers is formed under these conditions. A detailed computational investigation of the cyclization reaction mechanism suggests facile C-N bond formation in the radical cation leading to a 5-exo intermediate. Back-electron transfer from the DCA radical anion followed by barrierless intramolecular proton transfer leads to the final product. We argue that the final proton transfer step in the mechanism is responsible for the stereoselectivity observed in experiment. As a whole, this work provides new insights into the formation of complex heterocycles through oxime and oxime ether radical cation intermediates produced via PET. Moreover, it represents the first reported formation of isoindole N-oxides.

Visible-Light-Induced Cyclization/Aromatization of 2-Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives

A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed and provided unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the thiosulfonylation product of 2-vinyloxy arylalkyne was the key intermediate, and the additive disulfide played the role of hydrogen abstraction in the aromatization process to offer the desired product. This reaction presents a new reaction mode for the construction of polycyclic oxygen heterocycles.

Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds

Employing silver/rhodium relay catalysis strategy, an intramolecular electrophilic cyclization and C?H activation followed by cascade hydrogenation and reductive amination has been developed. The acylmethylated isoquinoline derivatives could be afforded with broad substrate scope in 23–88% yields, which could be further transformed to the core skeleton of hexahydrodibenzo[a,g]quinolizine as drug-candidates. Moreover, this reaction was achieved in a gram-scale. A reasonable reaction mechanism has been proposed based on a series of control and KIE experiments. (Figure presented.).

Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.

Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives

An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.

A Mild and Regioselective Synthesis of α-Fluoroketones via Gold and Selectfluor Partnership

An efficient, mild and rapid synthesis of α-fluoroketones has been developed, via a fruitful association between gold and Selectfluor starting from aldehyde-yne and alkynylaryl ketone derivatives. Several functionalized and synthetically highly valuable α-fluoroketones (21 compounds, up to 92%) were isolated in good to excellent yields via a remarkable regioselective oxyfluorination reaction in EtOH/H2O at room temperature. We have shed some light on parts of the mechanism by reacting diphenylacetylene and aldehyde-yne with or without Selectfluor. The reaction most presumably occurs via a sequential gold-catalyzed regioselective hydration followed by the α-fluorination reaction, but the presence of aldehyde moiety is crucial for the reactivity of alkyne function. The fluoroketones were efficiently transformed to 4-fluoroisoquinolines (9 compounds, 82–95%) of high pharmaceutical interest. (Figure presented.).

Chemo- and Regioselective Catalyst-Controlled Carbocyclization of Alkynyl Ketones: Rapid Synthesis of 1-Indanones and 1-Naphthols

A catalyst-controlled intramolecular carbocyclization of 2-alkynyl aryl ketones is presented. Under rhodium(III) catalysis, 1-indanones are formed through 5-exo-dig carbocyclizations with exclusive chemo-, regio- and stereoselectivity. When catalyzed by copper(I), 1-naphthols are obtained through 6-endo-dig carbocyclizations with exclusive chemo- and regioselectivity.