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Usage

Uses

Used in Pharmaceutical Industry:
3-naphthalen-2-yl-3-oxo-propanenitrile is used as a starting material for the synthesis of various pharmaceutical agents. Its unique structure allows for the development of new drugs with potential therapeutic applications, making it a valuable component in medicinal chemistry.
Used in Dye and Pigment Production:
In the dye and pigment industry, 3-naphthalen-2-yl-3-oxo-propanenitrile is utilized for the production of dyes and pigments. Its chemical properties contribute to the color and stability of these products, which are essential for various applications, including textiles, plastics, and printing inks.
Used in Material Science:
3-naphthalen-2-yl-3-oxo-propanenitrile also finds applications in material science. Its structural features can be incorporated into the development of new materials with specific properties, such as improved strength, durability, or optical characteristics.
Used as a Reagent in Chemical Research:
In the field of chemical research, 3-naphthalen-2-yl-3-oxo-propanenitrile serves as a reagent. It is employed in various chemical reactions and experiments, contributing to the advancement of scientific knowledge and the discovery of new chemical processes and compounds.

InChI:InChI=1/C13H9NO/c14-8-7-13(15)12-6-5-10-3-1-2-4-11(10)9-12/h1-6,9H,7H2

Upstream product

• 3007-91-8 ethyl-2-naphthoate 
• 75-05-8 acetonitrile 
• 876-27-7 4-chlorophenyl acetate 
• 144119-14-2 3-hydroxy-3-(naphthalen-2-yl)propanenitrile 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 612-55-5 2-iodonaphthalene 
• 13939-06-5 molybdenum hexacarbonyl 
• 2459-25-8 methyl naphthalene-2-carboxylate 
• 1592-38-7 2-Naphthalenemethanol 
• 7677-24-9 trimethylsilyl cyanide 
• 52119-18-3 1-(2-naphthalenyl)-1-(trimethylsilyloxy)ethylene 
• 78831-76-2 (E)-3-Chloro-3-naphthalen-2-yl-acrylonitrile 
• 32316-92-0 naphthalene-2-boronic acid 
• 109-77-3 malononitrile 

Downstream Products

• 52824-47-2 (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-naphthalen-2-yl-methanone 
• 56048-51-2 2-(2-naphthyl)benzothiazole 
• 1401051-85-1 2,3,9,10-tetraphenylanthra[1,9-bc]pyran-11-carbonitrile 
• 1401051-91-9 2,3,9,10-tetraphenylphenanthro[1,10-bc]pyran-11-carbonitrile 
• 334709-78-3 3-(naphthalen-2-yl)isoxazol-5-amine 

Relevant academic research and scientific papers

Transfer hydrogenation in water: Enantioselective, catalytic reduction of α-cyano and α-nitro substituted acetophenones

Catalytic reduction of α-substituted acetophenones under conditions involving asymmetric transfer hydrogenation in water is described. The reaction is conducted in water and open to air, and formic acid is used as reductant.

Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center

A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals were converted to C3- or C3,C5-chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.

Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions

A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles

A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.

Reaction of 1,3-Bis(het)arylmonothio-1,3-diketones with Sodium Azide: Regioselective Synthesis of 3,5-Bis(het)arylisoxazoles via Intramolecular N-O Bond Formation

An efficient new synthesis of 3,5-bis(het)arylisoxazoles, involving the reaction of 1,3-bis(het)arylmonothio-1,3-diketones with sodium azide in the presence of IBX catalyst, has been reported. The reaction proceeds at room temperature in high yields and is applicable to a broad range of substrates including the synthesis of 5-methyl-3-arylisoxazoles, a key subunit present in several β-lactamase-resistant antibiotics. A probable mechanism for the formation of isoxazoles has been suggested. A few of the 5-styryl/arylbutadienyl-3-(het)arylisoxazoles have also been synthesized by reacting the corresponding 1-(het)aryl-1-(methylthio)-4-(het)arylidene-but-1-en-3-ones with sodium azide at higher temperatures. The reaction of β-ketodithioesters with sodium azide is shown to furnish β-ketonitriles in good yields.

Synthesis of α-Ketoamides from β-Ketonitriles and Primary Amines: A Catalyst-Free Oxidative Decyanation–Amidation Reaction

AN oxidative decyanation–amidation of β-ketonitriles and primary amines readily occurs using hydrogen peroxide sodium carbonate adduct (Na2CO3·1.5H2O2), K2CO3, and 1,4-dioxane. This reactio

A Pd-catalyzed asymmetric allylic substitution cascade: Via an asymmetric desymmetrization for the synthesis of bicyclic dihydrofurans

A Pd-catalyzed asymmetric allylic substitution cascade of allylic meso-dicarbonates with 3-oxo-nitriles has been developed for the synthesis of chiral bicyclic dihydrofurans bearing two vicinal carbon stereocenters. The reaction proceeds via an asymmetric desymmetrization process with the desired products being obtained in high yields and with up to 97% ee. The reaction was performed on a gram-scale and the corresponding bicyclic dihydrofurans could undergo several transformations. The methodology provides an efficient synthetic route to biologically active chiral bicyclic dihydrofurans derivatives.

Substrate-controlled switchable asymmetric annulations to access polyheterocyclic skeletons

An unexpected domino process from Morita-Baylis-Hillman carbonates of isatins and acrylate and α-cyano-α,β-unsaturated ketones to deliver highly enantioenriched tetrahydrofuro[2′,3′:4,5]pyrano[2,3-b]indoles catalysed by cinchona-derived tertiary amines, involving α-regioselective cyclopropanation, ring-opening, and ring-closure cascade reactions, was disclosed. In contrast, spirooxindoles incorporating a cyclopentene motif were produced through [3+2] annulations by employing Morita-Baylis-Hillman carbonates from isatins and acrylonitrile under similar catalytic conditions. Density functional theory calculations were conducted to elucidate the novel domino process and the switchable annulation reactions.

Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

Copper-catalyzed Aerobic Oxidative coupling of Aromatic Alcohols and Acetonitrile to β-Ketonitriles

A practical, convenient, and cheap coppercatalyzed aerobic oxidative coupling of aromatic alcohols and acetonitrile to β-ketonitriles has been developed. The green C-C bond formation involving the loss of two hydrogen atoms from the corresponding two carbons, respectively, unlocks opportunities for markedly different synthetic strategies.