658-13-9

Basic information

• Product Name: (4-FLUORO-PHENYL)-OXO-ACETONITRILE
• Synonyms: 4-FLUOROBENZOYL CYANIDE;(4-FLUORO-PHENYL)-OXO-ACETONITRILE
• CAS NO: 658-13-9
• Molecular Formula: C₈H₄FNO
• Molecular Weight: 149.12
• Mol File: 658-13-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 220.826 °C at 760 mmHg
• Flash Point: 87.353 °C
• Appearance: /
• Density: 1.258 g/cm³
• Vapor Pressure: 0.111mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: (4-FLUORO-PHENYL)-OXO-ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-FLUORO-PHENYL)-OXO-ACETONITRILE(658-13-9)
• EPA Substance Registry System: (4-FLUORO-PHENYL)-OXO-ACETONITRILE(658-13-9)

Safety Data

• Hazardous Substances Data: 658-13-9(Hazardous Substances Data)

Usage

General Description

(4-FLUORO-PHENYL)-OXO-ACETONITRILE, also known as 4-Fluorophenylacetonitrile, is a chemical compound with the molecular formula C8H6FNO. It is a fluorinated aromatic compound that contains a nitrile functional group. (4-FLUORO-PHENYL)-OXO-ACETONITRILE is commonly used in the field of organic synthesis and pharmaceutical research as a building block for the synthesis of various pharmaceuticals and fine chemicals. It is also used in the production of agrochemicals and insecticides. The presence of the fluorine atom in the phenyl ring makes this compound valuable in a wide range of chemical reactions and applications.

InChI:InChI=1/C8H4FNO/c9-7-3-1-6(2-4-7)8(11)5-10/h1-4H

Upstream product

• 462-06-6 fluorobenzene 
• 1115-12-4 carbonyl cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 403-43-0 4-fluorobenzoyl chloride 
• 544-92-3 copper(I) cyanide 
• 459-22-3 4-fluorophenylacetonitrile 
• 74-90-8 hydrogen cyanide 
• 459-57-4 4-fluorobenzaldehyde 
• 133721-87-6 2-(4-fluorophenyl)-2-hydroxyacetonitrile 

Downstream Products

• 824-75-9 p-fluorobenzamide 
• 366-63-2 4-fluoro-N-phenylbenzamide 
• 2251-76-5 2-(4-fluorophenyl)-2-oxoacetic acid 
• 78482-21-0 2-(4-Fluoro-phenyl)-2-oxo-thioacetamide 
• 29681-98-9 p-fluorobenzoylacetone 
• 78482-28-7 5-(4-Fluoro-phenyl)-2,2-dimethyl-4-methylsulfanyl-2,5-dihydro-oxazol-5-ol 
• 401580-43-6 5-(4-fluorophenyl)-3-phenyl-1,2,4-oxadiazole 
• 1443017-22-8 5-(4-fluorophenyl)-3-(2-methoxyphenyl)-1,2,4-oxadiazole 
• 836662-41-0 5-(4-fluorophenyl)-3-(3-methoxyphenyl)-1,2,4-oxadiazole 
• 378217-59-5 5-(4-fluorophenyl)-3-(4-methoxyphenyl)-1,2,4-oxadiazole 
• 1443017-24-0 5-(4-fluorophenyl)-3-(2-nitrophenyl)-1,2,4-oxadiazole 
• 421581-70-6 5-(4-fluorophenyl)-3-(3-nitrophenyl)-1,2,4-oxadiazole 
• 96898-35-0 5-(4-fluorophenyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole 
• 1443017-31-9 3-cyclohexyl-5-(4-fluorophenyl)-1,2,4-oxadiazole 

Relevant articles and documents

Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction

Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.

Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex

Ruthenium-catalyzed dehydrogenation of cyanohydrins under acceptorless and base-free conditions was demonstrated for the first time in the synthesis of acyl cyanide. As opposed to the thermodynamically preferred elimination of hydrogen cyanide, the dehydrogenation of cyanohydrins could be kinetically controlled with ruthenium (II) bidentate phosphine complexes. The effects of the arene, phosphine ligands and counter anions were investigated in regard to catalytic activity and selectivity. Selective dehydrogenation can occur via β-hydride elimination with the experimentally observed [(alkoxide)Ru] complex. (Figure presented.).

Rh-Catalyzed Asymmetric Hydrogenation of 1,2-Dicyanoalkenes

A highly efficient enantioselective hydrogenation of 1,2-dicyanoalkenes catalyzed by the complex of rhodium and f-spiroPhos has been developed. A series of 1,2-dicyanoalkenes were successfully hydrogenated to the corresponding chiral 1,2-dicyanoalkanes under mild conditions with excellent enantioselectivities (up to 98% ee). This methodology provides efficient access to the asymmetric synthesis of chiral diamines.