6136-62-5

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Benzoylbenzonitrile is utilized as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and medicines. Its unique structure and reactivity allow it to be incorporated into complex molecular frameworks, enhancing the therapeutic potential of resulting compounds.
Used in Dye Production:
In the dye industry, 3-Benzoylbenzonitrile is employed as a starting material or intermediate in the production of various dyes. Its ability to participate in multiple types of chemical reactions facilitates the creation of a wide range of colorants used in textiles, printing, and other applications.
Used in Organic Synthesis:
3-Benzoylbenzonitrile is used as a reagent in organic synthesis, where it aids in the formation of new compounds through its participation in various chemical reactions. Its versatility makes it a valuable tool for chemists working to develop new organic molecules.
Used in Drug Development and Medicinal Chemistry:
Due to its biological activities, 3-Benzoylbenzonitrile has been studied for its potential use in drug development and medicinal chemistry. Its presence in the synthesis of compounds with therapeutic properties underscores its importance in the ongoing search for new and effective treatments for various diseases and conditions.

InChI:InChI=1/C14H9NO/c15-10-11-5-4-8-13(9-11)14(16)12-6-2-1-3-7-12/h1-9H

Upstream product

• 2835-78-1 3-amino benzophenone 
• 591-51-5 phenyllithium 
• 1711-11-1 3-cyanobenzoyl chloride 
• 13428-06-3 3-(hydroxy(phenyl)methyl)benzonitrile 
• 6952-59-6 3-cyanobromobenzene 
• 98-88-4 benzoyl chloride 
• 71-43-2 benzene 
• 1877-72-1 3-Cyanobenzoic acid 
• 98-80-6 phenylboronic acid 
• 69113-59-3 3-iodobenzonitrile 
• 24964-64-5 3-Cyanobenzaldehyde 
• 93717-55-6 3-benzylbenzonitrile 
• 868526-00-5 C₇H₄ClNZn 
• 100-47-0 benzonitrile 

Downstream Products

• 13428-06-3 3-(hydroxy(phenyl)methyl)benzonitrile 
• 73831-67-1 3-(1-Hydroxy-2,2-dimethyl-1-phenyl-propyl)-benzonitrile 
• 73831-68-2 4-tert-butyl-3-cyano-benzophenone 
• 74672-16-5 [3-((phenylmethyl)phenyl)methyl]amine 
• 197792-35-1 C₁₈H₁₅NO₂ 
• 6136-68-1 3-acethylbenzonitrile 
• 21204-86-4 m-benzoylbenzoic acid methyl ester 
• 579-18-0 3-benzoylbenzoic acid 
• 101168-85-8 1-[3-(1-hydroxy-1-phenyl-ethyl)-phenyl]-ethanone 
• 13391-41-8 3-(alpha-chlorobenzyl)benzonitrile 

Relevant academic research and scientific papers

Novelmeta-benzothiazole and benzimidazole functionalised POCOP-Ni(ii) pincer complexes as efficient catalysts in the production of diarylketones

The synthesis of four novel non-symmetric Ni(ii)-POCOP pincer complexesmeta-functionalized with either benzothiazole or benzimidazole at the central aryl ring is described. All complexes were fully characterised in solution by various analytical techniques and the molecular structures in the solid state of complexes1b,2aand2bwere unequivocally determined by single crystal X-ray diffraction analysis. In addition, the Ni(ii)-POCOP pincer complexes were efficiently used as catalysts in the synthesis of diarylketones by cross-coupling reactions of functionalized benzaldehydes and boronic acid derivatives under relatively mild conditions. An important aspect of this transformation is the dependence on the steric properties of the donor groups (OPR2) of the pincer ligands, the more active compounds having the phosphinitos bearing isopropyl groups (1aand2a) than those containingtert-butyl substituents (1band2b).

Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N?C Cleavage

The direct transition-metal-free acylation of amides with functionalized Grignard reagents by highly chemoselective N?C cleavage under kinetic control has been accomplished. The method offers rapid and convergent access to functionalized biaryl ketones through transient tetrahedral intermediates. The direct access to functionalized Grignard reagents by in situ halogen–magnesium exchange promoted by the versatile turbo-Grignard reagent (iPrMgCl?LiCl) permits excellent substrate scope with respect to both the amide and Grignard coupling partners. These reactions enable facile, operationally simple and chemoselective access to tetrahedral intermediates from amides under significantly milder conditions than chelation-controlled intermediates. This novel direct two-component coupling sets the stage for using amides as acylating reagents in an alternative paradigm to the metal-chelated approach, acyl metals and Weinreb amides.

Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic controlvs.kinetic control ofN,N-Boc2-amides

A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents is reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method is highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives. Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N-C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest.

Acyl radicals from α-keto acids using a carbonyl photocatalyst: Photoredox-catalyzed synthesis of ketones

Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridylstabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol is compatible with a wide range of functional groups.

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones

We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.

Polymer-incarcerated palladium-catalyzed facile: In situ carbonylation for the synthesis of aryl aldehydes and diaryl ketones using CO surrogates under ambient conditions

In this existing work, an efficient polymer-supported palladium catalyst, a furfurylamine-functionalized Merrifield complex of palladium [Pd@(Merf-FA)], was synthesized and characterized, showing excellent catalytic activity towards in situ carbonylation reactions using carbon monoxide surrogates like formic acid and chloroform. Herein, we examined the catalytic activity of the Pd@(Merf-FA) catalyst for the formylation of aryl iodides and carbonylative Suzuki-Miyaura coupling reactions. The Pd@(Merf-FA) catalyst was systematically characterized by several techniques like HRTEM, elemental mapping, PXRD, TGA-DTA, FESEM, UV-vis, EDAX, CHN and AAS analysis. The catalyst is highly recyclable, able to be recycled up to six times without showing any significant decrease in catalytic activity. The [Pd@(Merf-FA)] catalyst proved to be more efficient compared to the corresponding homogeneous palladium catalyst. In addition, the leaching experiment of the synthesized catalyst was studied, which showed that negligible leaching of metal occurred from the polymeric support.

Palladium-Catalyzed Ligand-Free Decarboxylative Coupling of α- Oxocarboxylic Acid with Aryl Diazonium Tetrafluoroborate: An Access to Unsymmetrical Diaryl Ketones

Diaryl ketones are of much importance in organic synthesis as versatile intermediates and in industry for their useful properties. A mild and efficient palladium-catalyzed traditional ligand-free decarboxylative coupling of aryl α-keto carboxylic acid with aryl diazonium fluoroborate has been developed. A series of unsymmetrical diaryl ketones has been synthesized in moderate to good yields using this procedure. A radical pathway involving the acyl radical has been suggested.

Acyl and Decarbonylative Suzuki Coupling of N-Acetyl Amides: Electronic Tuning of Twisted, Acyclic Amides in Catalytic Carbon-Nitrogen Bond Cleavage

We report the Pd-catalyzed acyl and the Ni-catalyzed biaryl Suzuki-Miyaura cross-coupling of N-acetyl-amides with arylboronic acids by selective N-C(O) cleavage. Activation of the amide bond by N-acylation provides electronically destabilized, acyclic, nonplanar amide, which readily undergoes cross-coupling with a wide range of boronic acids to produce biaryl ketones or biaryls in a highly efficient manner. Most crucially, the presented results introduce N-acetyl-amides as reactive acyclic amides in the emerging manifold of transition-metal-catalyzed amide cross-coupling. The scope and origin of high selectivity are discussed. Mechanistic studies point to remodeling of amidic resonance and amide bond twist as selectivity determining features in a unified strategy for cross-coupling of acyclic amides. Structural studies, mechanistic investigations as well as beneficial effects of the N-acyl substitution on cross-coupling of amides are reported.

Synthesis of some ketones via nano-nickel oxide catalyzed acylation of arylzinc reagents; strategy involving the use of mixed (methyl)(aryl)zincs

Nano-NiO catalyzed acylation of mixed (methyl)(aryl)zincs with aromatic acyl halides in THF at room temperature provides a new facile route for aryl–aroyl coupling. Among NiCl2 .L2 and NiCl2 .L (L = monodentate and bidentate phosphine ligand) catalysts, the lower catalyst loading of NiCl2 (dppf) may seem attractive; however, nano-NiO, being the lowest cost catalyst, is more favorable for aroylation of (methyl)(aryl)zincs. This procedure also provides a supplement to Cu and Pd catalyzed acylation of diorganozincs.

CO2-Catalyzed oxidation of benzylic and allylic alcohols with DMSO

CO2-catalyzed transition-metal-free oxidation of alcohols has been achieved. Earlier, several methodologies have been explored for alcohol oxidations based on transition-metal catalysts. However, owing to the cheaper price, easy separation and nontoxicity, transition-metal-free systems are in high demand to the pharmaceutical industries. For this reason, various primary and secondary alcohols have been selectively oxidized to the corresponding carbonyl compounds using CO2 as a catalyst in the presence of different functional groups such as nitrile, nitro, aldehyde, ester, halogen, ether, and so on. At the end, transition-metal-free syntheses of pharmaceuticals have also been achieved. Finally, the role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments and DFT calculations.