756489-25-5

Basic information

• Product Name: 4-(4-FLUOROPHENYL)-4-OXOBUTANENITRILE
• Synonyms: 4-(4-FLUOROPHENYL)-4-OXOBUTANENITRILE;4-(4-FLUOROPHENYL)-4-OXOBUTYRONITRILE;SALOR-INT L481998-1EA
• CAS NO: 756489-25-5
• Molecular Formula: C10H8FNO
• Molecular Weight: 177.18
• Mol File: 756489-25-5.mol

Chemical Properties

• Boiling Point: 340.3°C at 760 mmHg
• Flash Point: 159.6°C
• Appearance: /
• Density: 1.168g/cm³
• Vapor Pressure: 8.7E-05mmHg at 25°C
• Refractive Index: 1.511
• CAS DataBase Reference: 4-(4-FLUOROPHENYL)-4-OXOBUTANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-FLUOROPHENYL)-4-OXOBUTANENITRILE(756489-25-5)
• EPA Substance Registry System: 4-(4-FLUOROPHENYL)-4-OXOBUTANENITRILE(756489-25-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 756489-25-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H8FNO/c11-9-5-3-8(4-6-9)10(13)2-1-7-12/h3-6H,1-2H2

Upstream product

• 403-43-0 4-fluorobenzoyl chloride 
• 107-13-1 acrylonitrile 
• 1765-93-1 4-fluoroboronic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 110-61-2 butanedinitrile 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 75-05-8 acetonitrile 
• 147164-48-5 1-(4-fluorophenyl)ethenyl acetate 
• 706-06-9 3-(4-flurophenyl)prop-2-ynoic acid 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 405-99-2 para-fluorostyrene 
• 105-56-6 ethyl 2-cyanoacetate 

Relevant articles and documents

Facile Synthesis of γ-Ketonitriles in Water via C(sp2)–H Activation of Aromatic Aldehydes over Cu?g-C3N4 under Visible-Light

A facile C(sp2)–H activation of aldehyde under visible-light conditions using Cu?g-C3N4 as photocatalyst and water as solvent is reported. The envisaged method involves photocatalytic intermolecular Stetter reaction using

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.

A Novel Ketonitrile Synthesis by Palladium-Catalyzed Carbonylative Coupling Reactions of Amides with Arylboronic Acids

A novel, efficient, and simple procedure to synthesize diverse ketonitriles by palladium-catalyzed Suzuki coupling of amides through N–C cleavage has been developed. This procedure features mild conditions, a broad substrate scope, and easily prepared substrates, providing a simple and efficient access to a variety of ketonitriles.

Ag2CO3-mediated direct functionalization of alkyl nitriles: Facile synthesis of γ-ketonitriles through nitrile alkylation of enol acetates

Direct C(sp3)-H functionalization of alkyl nitriles is a low toxic and facile route to nitrile-containing compounds. In this research, the Ag2CO3-mediated nitrile methylenation of enol acetates is developed to prepare γ-ketonitriles through the direct C(sp3)-H oxidative functionalization of acetonitrile. A radical pathway is proposed, and acetonitrile serves both as solvent and CN-containing radical source.

Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of ?-Diketones and ?-Ketonitriles

A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)-H bond functionalization to construct new C-C bonds and C-O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to ?-diketones and ?-ketonitriles. A possible mechanism is proposed.

Copper(i)-catalyzed ring-opening cyanation of cyclopropanols

A copper(i)-catalyzed ring-opening cyanation of cyclopropanols was developed. The reaction provides an alternative method to achieve β-cyano ketones efficiently. This reaction exhibits good functional group compatibility under mild conditions and can be scaled up to the gram scale. Preliminary mechanistic studies suggest that the reaction might go through a free radical process.

Chemoselective Access to γ-Ketoesters with Stereogenic Quaternary α-Center or γ-Keto Nitriles by Aerobic Reaction of α-Cyanoesters and Styrenes

Chemoselective access to either γ-ketoesters with a quaternary all-carbon α-stereogenic center or γ-keto nitriles is described by copper-catalyzed aerobic reaction of styrenes with α-cyanoesters. Formal oxo-enolation or oxo-cyanomethylation of styrenes is achieved via a sequence of addition of enolate (or cyanomethyl) radical to olefin and oxidation of the resulting radical adduct. This method starts from abundant and cheap feedstock under aerobic conditions, without any prefunctionalization or the production of stoichiometric metal salts waste, making it very attractive for practical use.

Preparation γ - par phenyle and γ - ketoester method (by machine translation)

The invention relates to a process for preparing γ - par phenyle and γ - ketoester method, characterized in that comprises the following experimental procedure: catalyst/ligand/additive under the catalytic action of, in the environment of oxygen, with the α - cyano ester substituted styrene mixed solution for 60 - 100 °C oil bath pot reaction 12 - 20 h; cooling after reaction to the room temperature, by extraction, washing, drying and chromatography, to obtain the product γ - par phenyle and γ - ketoester. The invention of each reaction raw material, catalyst, ligand, additive and solvent are industrial commodities, simple and easy to obtain, the price is cheap, and performance is quite stable, does not need special storage conditions, the operation is convenient. The invention has advantages of low cost, high yield, the process is simple, and less pollution and the like. (by machine translation)

Unactivated C(sp3)-H Bond Functionalization of Alkyl Nitriles with Vinylarenes and Mechanistic Studies

The first example of a metal-free unactivated C(sp3)-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp3)-H bond functionalization of azodiisobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate γ-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway.

Stetter reaction in room temperature ionic liquids and application to the synthesis of haloperidol

Imidazolium-type room temperature ionic liquids (RTILs) have been used for the Stetter reaction, affording the desired 1,4-dicarbonyl compounds in good yields. Thiazolium salts and Et3N are efficient catalysts for this reaction performed in ionic liquid. The possibility to recycle and reuse the solvent has been demonstrated, although it was not possible to recycle the thiazolium catalyst. This method was used in the total synthesis of haloperidol.