73013-48-6

Usage

Uses

Used in Pharmaceutical Industry:
(2-Cyanophenyl)acetone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to participate in multiple chemical reactions, contributing to the development of a broad spectrum of medicinal products.
Used in Fine Chemicals Industry:
In the fine chemicals sector, (2-Cyanophenyl)acetone is utilized as an intermediate due to its reactivity in acylation, reduction, and oxidation processes, which allows for the creation of a wide range of specialty chemicals.
Safety Precautions:
It is crucial to handle (2-Cyanophenyl)acetone with care, as it is a flammable substance. Additionally, it can cause irritation to the eyes, skin, and respiratory system, necessitating proper safety measures during its use and storage.

InChI:InChI=1/C10H9NO/c1-8(12)6-9-4-2-3-5-10(9)7-11/h2-5H,6H2,1H3

Upstream product

• 873-32-5 2-Chlorobenzonitrile 
• 24262-31-5 acetone enolate ion 
• 100-47-0 benzonitrile 
• 67-64-1 acetone 
• 2042-37-7 o-cyanobromobenzene 
• 123-54-6 acetylacetone 
• 529-19-1 2-Methylbenzonitrile 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 108-22-5 Isopropenyl acetate 
• 1885-29-6 anthranilic acid nitrile 
• 7468-67-9 o-formylbenzonitrile 
• 55165-45-2 2-cyano-benzenediazonium tetrafluoroborate 
• 75-36-5 acetyl chloride 

Downstream Products

• 1447698-77-2 (2S,3S)-2-(2-hydroxypentan-3-yl)benzonitrile 
• 1447698-78-3 (2S,3S)-2-(2-hydroxyhex-5-en-3-yl)benzonitrile 
• 1447698-95-4 2-(3-oxobutan-2-yl)benzonitrile 
• 1447698-72-7 (2S,3S)-2-(3-hydroxybutan-2-yl)benzonitrile 
• 1447698-31-8 2-(2-oxopentan-3-yl)benzonitrile 
• 1447698-34-1 2-(2-oxohex-5-en-3-yl)benzonitrile 
• 1447698-18-1 2-(3-oxobutan-2-yl)benzonitrile 

Relevant academic research and scientific papers

Nickel-Catalyzed Mono-Selective α-Arylation of Acetone with Aryl Chlorides and Phenol Derivatives

The challenging nickel-catalyzed mono-α-arylation of acetone with aryl chlorides, pivalates, and carbamates has been achieved for the first time. A nickel/Josiphos-based catalytic system is shown to feature unique catalytic behavior, allowing the highly selective formation of the desired mono-α-arylated acetone. The developed methodology was applied to a variety of (hetero)aryl chlorides including biologically relevant derivatives. The methodology has been extended to the unprecedented coupling of acetone with phenol derivatives. Mechanistic studies allowed the isolation and characterization of key Ni0 and NiII catalytic intermediates. The Josiphos ligand is shown to play a key role in the stabilization of NiII intermediates to allow a Ni0/NiII catalytic pathway. Mechanistic understanding was then leveraged to improve the protocol using an air-stable NiII pre-catalyst.

UiO-66 microcrystals catalyzed direct arylation of enol acetates and heteroarenes with aryl diazonium salts in water

UiO-66 is a classic Metal–organic framework (MOF) that constructed by zirconium cations and terephthalate with high chemical and thermal stability. Using pristine UiO-66 nanocrystals as the catalysts, the carbon–carbon bond formation based on denitrogenat

Atroposelective Arene Formation by Carbene-Catalyzed Formal [4+2] Cycloaddition

Atroposelective arene formation is an efficient method to build axially chiral molecules with multi-substituted arenes. Reported here is an organocatalyzed atroposelective arene formation reaction by an N-heterocyclic carbene (NHC) catalyzed formal [4+2] cycloaddition of conjugated dienals and α-aryl ketones. This study expands the synthetic potential of NHC organocatalysis and provides a competitive pathway for the synthesis of axially chiral ligands, catalysts, and other functional molecules.

Domino Synthesis of Benzo-Fused β,γ-Unsaturated Ketones from Alkenylboronic Acids and N-Tosylhydrazone-Tethered Benzonitriles

The transition-metal-free domino reaction between alkenylboronic acids and N-tosylhydrazones from o-(2-oxoalkyl)- and o-(3-oxoalkyl)benzonitriles leads to β, γ-unsaturated indanones and tetralones featuring an α-"all-carbon" quaternary center. The employment of derivatives of α-substituted cyclopentanones and cyclohexanones led to the stereoselective preparation of β, γ-unsaturated tetrahydrocyclopenta[a]inden-8(1H)-ones, hexahydrofluorenones, and hexahydroanthracenones as cis-fused single stereoisomers. A domino sequence involving diazo compound formation/reductive alkenylation/1,3-borotropic rearrangement/intramolecular bora-aza-ene reaction is proposed to justify the formation of the products as well as the stereoselectivity.

C-H arylation reactions through aniline activation catalysed by a PANI-g-C3N4-TiO2 composite under visible light in aqueous medium

A PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for radical C-H arylation reactions. The arylation process involved coupling of in situ generated aryl diazonium salts from aniline with heteroarenes, enol acetates or benzoquinones under visible light in aqueous medium or pure water. A broad range of substrates survived the reaction conditions to provide the desired products in moderate to good yields. Scale-up (10 mmol) synthesis was also achieved. This semiconductor photocatalyst showed good photocatalytic performance and stability. Recycle studies showed that this composite could be readily recovered and a slight decrease in the catalytic activity was observed after ten consecutive runs.

Salicylic Acid-Catalyzed Arylation of Enol Acetates with Anilines

α-Aryl ketones are both structure moieties commonly found in bioactive compounds and versatile synthetic intermediates for the preparation of drug-like molecules. An operationally simple and scalable protocol has been developed to prepare α-aryl ketones from readily available aromatic amines and enol acetates (or silyl enol ethers). This metal-free methodology features the use of salicylic acid as a convenient catalyst to promote the formation of aryl radicals from in-situ generated aryl diazonium salts, without demanding thermal or photochemical activation. The mild reaction conditions used are compatible with anilines substituted with diverse functionalities. Structural elaboration of some prepared α-aryl ketones was accomplished to illustrate their usefulness as building blocks. (Figure presented.).

Visible-light-mediated α-arylation of enol acetates using aryl diazonium salts

Visible light mediates efficiently the α-arylation of enol acetates by aryl diazonium salts under mild conditions using [Ru(bpy)3]Cl 2 as a photoredox catalyst. The broad scope of the reaction toward various diazonium salts and enol acetates was explored. The application of this reaction in the concise synthesis of 2-substituted indoles was demonstrated

A practical synthesis of α-aryl methyl ketones via a transition-metal-free Meerwein arylation

We report herein a simple, scalable, transition-metal-free approach to the synthesis of α-aryl methyl ketones from diazonium tetrafluoroborate salts under mild conditions. This methodology uses easily accessible and nontoxic starting material and was applied to the multi-kilogram-scale preparation of 1-(3-bromo-4-methylphenyl)propan-2-one.

Chemoenzymatic synthesis of (S)-8-O-methylmellein by Candida parapsilosis carbonyl reductase

A screening of various orthosubstituted 2-oxopropylbenzene derivatives with carbonyl reductases and alcohol dehydrogenases, respectively, revealed that compounds containing ortho-substituents with only little steric demand are feasible substrates. (S)-8-O-Methylmellein (1) was synthesized by stereoselective enzymatic reduction of 2-methoxy-6-(2-oxopropyl)benzonitrile (5i) with Candida parapsilosis carbonyl reductase as the key step, and completed by a one-step hydrolysis and intramolecular cyclization.