59824-23-6

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Cyanophenyl)acetophenone is used as an intermediate in the synthesis of pharmaceuticals for its ability to facilitate the creation of complex organic compounds that can be utilized in developing new drugs.
Used in Organic Synthesis:
As a reagent, 2-(4-Cyanophenyl)acetophenone is used in organic synthesis reactions to produce a variety of chemical compounds, contributing to the development of new materials and substances.
Used in Research and Development:
In the fields of medicinal and pharmaceutical chemistry, 2-(4-Cyanophenyl)acetophenone is employed as a building block for the research and development of novel chemical entities, potentially leading to breakthroughs in drug discovery and chemical innovation.

InChI:InChI=1/C15H11NO/c16-11-13-8-6-12(7-9-13)10-15(17)14-4-2-1-3-5-14/h1-9H,10H2

Upstream product

• 5462-71-5 4-cyanophenylacetic acid 
• 93-89-0 benzoic acid ethyl ester 
• 104-85-8 para-methylbenzonitrile 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 623-00-7 4-bromobenzenecarbonitrile 
• 17763-67-6 Phenyl triflate 
• 129126-51-8 N,N-dimethyl-2-[(1-phenyl)ethenyloxy]ethanamine 
• 100-39-0 benzyl bromide 
• 17201-43-3 4-cyanobenzyl bromide 
• 74-89-5 methylamine 
• 201230-82-2 carbon monoxide 
• 874-86-2 4-cyanobenzyl chloride 
• 4747-13-1 α-methoxystyrene 
• 3058-39-7 4-iodobenzonitrile 

Downstream Products

• 346623-13-0 α'-oxo-bibenzyl-4-carboxylic acid 
• 898776-62-0 ethyl 4-(2-oxo-2-phenylethyl) benzoate 
• 855469-68-0 4-(1-benzoyl-propyl)-benzoic acid 
• 1286715-76-1 C₁₈H₁₆N₂O 
• 1283117-51-0 4-(4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidin-5-yl)benzonitrile 
• 5925-68-8 (S)-methyl thiobenzoate 
• 1387574-33-5 octyl p-cyanophenylmethyl ketone 
• 90013-81-3 4-<(2-Thienylcarbonyl)methyl>benzonitril 
• 62066-32-4 4-[2-(4-methoxyphenyl)-2-oxoethyl]benzonitrile 
• 62066-31-3 4-[2-(4-chlorophenyl)-2-oxoethyl]benzonitrile 
• 62044-21-7 4-(2-oxopentyl)benzonitrile 
• 1387574-36-8 4-[2-(3,5-dimethoxyphenyl)-2-oxoethyl]benzonitrile 
• 1387574-38-0 4-(2-oxo-3-cyclohexylpropyl)benzonitrile 
• 1387574-32-4 4-[2-oxo-2-(2-furanyl)ethyl]benzonitrile 

Relevant academic research and scientific papers

Photoinduced Cross-Coupling of Aryl Iodides with Alkenes

A protocol for photoinduced cross-coupling of aryl iodides having polar π-functional groups or elongated π-conjugation with alkenes has been developed. The radical cascade mechanism involving generation of aryl radicals via C-I bond homolysis of photoexcited aryl iodides and their subsequent addition to alkenes is proposed. The method enables iodide-selective cross-coupling over other halogen leaving groups with functional group compatibility on both arene and alkene motifs.

PtO2/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups

A highly efficient PtO2/PTSA catalyst system for the hydration of a wide array of alkynes was developed. This method proved to be compatible with a large range of functional groups and the ketone products were obtained in high yields. The scope of this methodology was also extended to the synthesis of 3-Aryl-isochromenones,-indoles and-benzofurans.

A family of low molecular-weight, organic catalysts for reductive C-C bond formation

Hydrazines form a new family of low molecular-weight reducing agents for diazonium salts. Using only small amounts of hydrazine catalyst, the coupling of diazonium salts to a variety of reactive partners has been achieved, without the requirement for either metal adjuvants or irradiation with visible or ultraviolet light. The generality of the concept proposed herein as well as its advantages in the preparative scale is outlined and discussed.

Copper(II)triflate promoted highly chemoselective rearrangement of chalcone epoxides to β-keto aldehydes

Highly chemoselective rearrangement of chalcone epoxides to β-keto aldehydes using catalytic amount of Cu(OTf)2 (1 mol%) is presented. Copper(II)triflate is a relatively cheap, inexpensive and commercially available catalyst. In this rearrangement selective migration of the acyl group takes place. The presence of an electron donating group on either of the phenyl rings favors the reaction. However, the presence of an electron withdrawing CN group leads to the corresponding β-keto aldehyde, along with an aryl ketone which is obtained through deformylation of the primary product.

An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal SRN1 reactions

Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electron transfer process to form new C-C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse 2-aryl-1- phenylethanones can be prepared by the direct α-arylation of acetophenone with different haloarenes. The ketone enolate anion is generated by deprotonation with tBuOK in DMSO and the reaction is carried out in a closed microwave vessel at 70-100°C for 10 min. This simple procedure also allows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ring closure reactions, with moderate to excellent substitution yields. This journal is the Partner Organisations 2014.

Palladium-catalyzed carbonylative negishi-type coupling of aryl iodides with benzyl chlorides

Do the competition: The synthesis of 1,2-diarylethanones has been accomplished using the palladium-catalyzed coupling of aryl iodides and CO/benzyl chlorides or benzoyl chlorides. These reactions proceed smoothly in the presence of zinc powder to afford the products in moderate to excellent yields.

Regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles via [3,3] or [1,3] rearrangements of O-vinyl oximes

The regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles has been achieved via [3,3] and [1,3] sigmatropic rearrangements of O-vinyl oximes, respectively. Iridium-catalyzed isomerization of easily prepared O-allyl oximes enables rapid access to O-vinyl oximes. The regioselectivity of pyrrole formation can be controlled by either the identity of the α-substituent or through the addition of an amine base. When enolization is favored, a [3,3] rearrangement followed by a Paal-Knorr cyclization provides a 2,3,4-trisubstituted pyrrole; when enolization is disfavored, a [1,3] rearrangement occurs prior to enolization to produce a 2,3,5-trisubstituted pyrrole after cyclization. Optimization and scope of the O-allyl oxime isomerization and subsequent pyrrole formation are discussed and mechanistic pathways are proposed. Conditions are provided for selecting either the [3,3] rearrangement or the [1,3] rearrangement product with β-ester O-allyl oxime substrates.

Palladium-catalyzed carbonylative suzuki coupling of benzyl halides with potassium aryltrifluoroborates in aqueous media

A general palladium-catalyzed carbonylative cross-coupling reaction of benzyl chlorides with potassium aryltrifluoroborates in water has been developed. Applying this improved methodology 16 different 1,2-diarylethanones have been synthesized in 40-89% yield. Copyright

NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS

The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

Heck reactions of α- or β-substituted enol ethers with aryl bromides catalysed by a tetraphosphane/palladium complex - Direct access to acetophenone or 1-arylpropanone derivatives

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphanylmethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Heck reaction of α- and β-substituted enol ethers with aryl bromides. The arylation of 1-phenyl-1-(trimethylsilyloxy) ethylene led directly to the 2-aryl-1-phenylethanones. Similar reaction rates were observed with electron-rich, electron-deficient or sterically congested aryl bromides. Heck reaction with benzyl isopropenyl ether gave a mixture of isomers. However, this mixture gave selectively the 1-arylpropanones after hydrolysis. Employing β-methoxystyrene, 3-ethoxyacrylonitrile or methyl 3-methoxyacrylate, the regioselective α-arylation of these enol ethers was observed in all cases, but mixtures of (Z) and (E) isomers were generally obtained, which in many cases yielded a single ketone product after acid treatment. The stereoselectivity of this reaction depends on steric and electronic factors, and better stereoselectivities in favour of (Z) isomers were observed with electron-rich or sterically congested aryl bromides. Higher yields were obtained for this reaction with electron-rich or sterically congested aryl bromides than with electron-poor aryl bromides. These observations suggest that the rate-limiting step of the catalytic cycle is not the oxidative addition of the aryl bromide to the palladium complex with these substituted enol ethers. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.