186297-56-3

Basic information

• Product Name: Ethanone, 2-fluoro-1-[4-(trifluoromethyl)phenyl]- (9CI)
• Synonyms: Ethanone, 2-fluoro-1-[4-(trifluoromethyl)phenyl]- (9CI)
• CAS NO: 186297-56-3
• Molecular Formula: C₉H₆F₄O
• Molecular Weight: 206.1369528
• Product Categories: ACETYLHALIDE
• Mol File: 186297-56-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethanone, 2-fluoro-1-[4-(trifluoromethyl)phenyl]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 2-fluoro-1-[4-(trifluoromethyl)phenyl]- (9CI)(186297-56-3)
• EPA Substance Registry System: Ethanone, 2-fluoro-1-[4-(trifluoromethyl)phenyl]- (9CI)(186297-56-3)

Safety Data

• Hazardous Substances Data: 186297-56-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 383-53-9 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone 
• 188912-47-2 trimethyl((1-(4-(trifluoromethyl)phenyl)vinyl)oxy)silane 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 1046785-19-6 1-(2-fluoro-1,1-dimethoxyethyl)-4-(trifluoromethyl)benzene 
• 503-20-8 fluoroacetonitrile 
• 402-43-7 p-trifluoromethylphenyl bromide 

Downstream Products

• 1073056-10-6 (R)-2-fluoro-1-(4-(trifluoromethyl)phenyl)ethanol 
• 197577-63-2 1-(1-Chloro-2-fluoro-ethyl)-4-trifluoromethyl-benzene 

Relevant articles and documents

Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation

Cesium carbonate (Cs2CO3)-mediated decarboxylative fluorination of β-ketoacids using NFSI in the MeCN/H2O mixed solvent system affords α-fluoroketones with a broad scope. Both electron-rich and electron-deficient α-non-substituted β-ketoacids are amenable to this protocol. The mechanistic study indicates that the reaction proceeds through electrophilic fluorination followed by decarboxylation, which is different from the decarboxylative fluorination of normal carboxylic acids.

Microwave assisted fluorination: an improved method for side chain fluorination of substituted 1-arylethanones

A two-step, one-pot microwave (MW) assisted fluorination of 1-arylethanones to their corresponding 1-aryl-2-fluoroethanones has been developed. The first step utilises Selectfluor as a fluorinating agent in methanol forming 1-aryl-2-fluoroethanones and their corresponding dimethyl acetals. In the second step, water is added and Selectfluor acts as a Lewis acid in the hydrolytic cleavage of the dimethyl acetals. Compared to the thermal synthesis, the MW assisted method leads to a reduction in reaction time both in the fluorination and for the dimethyl acetal cleavage. Moreover, the one-pot procedure reduces reagent and solvent consumption. The method is best suited for the preparation of 1-aryl-2-fluoroethanones containing substituents that deactivates electrophilic aromatic substitution, however highly electron deficient ketones such as 1-(3,5-dinitrophenyl)ethanone reacts more slowly. Reactions using electron rich aromatic ketones had a low regioselectivity, and also produced fluoroaromatic products.

Electrophilic and nucleophilic side chain fluorination of para-substituted acetophenones

para-Substituted α-fluoroacetophenones have been synthesised by three different routes. Electrophilic fluorination of trimethylsilyl enol ethers of acetophenones using Selectfluor (F-TEDA-BF4, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis-(tetrafluoroborate)) gave high to moderate yield depending on the electronic properties of the substituents. F-TEDA-BF4 mediated fluorination of acetophenones in methanol resulted in a mixture of α-fluoroacetophenones and the corresponding 2-fluoro-1,1-dimethyl acetals. The dimethyl acetals were hydrolysed using trifluoroacetic acid in water to maximise the yield of the product. Nucleophilic fluorination of α-bromoacetophenones using tetrabutylammonium hydrogen bifluoride (TBABF) led to moderate yield when having electron-donating substituents, whereas low yields were experienced when more electron-withdrawing substituents were introduced.