655-32-3

Usage

Uses

Used in Pharmaceutical Industry:
2,2,2,4'-TETRAFLUOROACETOPHENONE is used as a key intermediate in the stereoselective synthesis of trifluoromethyl-substituted 2H-furan-amines. These compounds are of significant interest due to their potential applications as pharmaceutical agents, particularly in the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
2,2,2,4'-TETRAFLUOROACETOPHENONE is also utilized as a building block in the synthesis of agrochemicals, such as insecticides and herbicides. The introduction of the trifluoromethyl group into these molecules can enhance their biological activity and selectivity, leading to more effective and environmentally friendly products.

Upstream product

• 352-13-6 4-flourophenylmagnesium bromide 
• 76-05-1 trifluoroacetic acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 122499-13-2 1-iodo-2,5-dioxa-1,3,3,4,6,6,7,7,8,8,8-undecafluoro-1,4-bis(trifluoromethyl)octane 
• 2923-17-3 lithium trifluoroacetate 
• 407-25-0 trifluoroacetic anhydride 
• 360-92-9 N,N-diethyl-2,2,2-trifluoroacetamide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 16184-83-1 O₂NCF₂C(4-F-C₆H₄)(OH)CF₃ 
• 74671-98-0 4'-fluoro-trifluoroacetophenone 
• 462-06-6 fluorobenzene 
• 383-63-1 ethyl trifluoroacetate, 
• 459-57-4 4-fluorobenzaldehyde 
• 17556-41-1 2,2,2-trifluoro-1-(4-fluorophenyl)ethanol 

Downstream Products

• 1979-54-0 2-p-Fluorphenylpentafluorpropen 
• 26029-55-0 1-Fluoro-4-(2,2,2-trifluoro-1-trifluoromethyl-ethyl)-benzene 
• 19302-04-6 1-((Z)-2-Chloro-2-fluoro-1-trifluoromethyl-vinyl)-4-fluoro-benzene 
• 19302-05-7 1-((E)-2-Chloro-2-fluoro-1-trifluoromethyl-vinyl)-4-fluoro-benzene 
• 74671-95-7 C₁₄H₁₆F₄N₂O 
• 97939-17-8 C₂₃H₂₉F₄N₂OP 
• 97939-27-0 2,2-di-tert-butyl-2-chloro-4-(p-fluorophenyl)-4-(trifluoromethyl)-1,2λ⁵-oxaphosphetane 
• 17556-41-1 2,2,2-trifluoro-1-(4-fluorophenyl)ethanol 
• 23516-79-2 4-(trifluoroacetyl)aniline 
• 123685-61-0 2,2,2-trifluoro-1-<4-(2-propynylamino)phenyl>ethanone 
• 2396-11-4 4-fluoro(pentafluoroethyl)benzene 
• 74671-98-0 4'-fluoro-trifluoroacetophenone 
• 173951-91-2 4-(ethylamino)trifluoroacetophenone 
• 75822-12-7 4-methylamino-α,α,α-trifluoroacetophenone 

Relevant academic research and scientific papers

Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF3-β-disubstituted nitroalkene was favorable.

REACTIVE EXTRACTION OF WATER

Described herein are methods and compounds for extracting water from an aqueous solution. For example, some embodiments include method for extracting water from an aqueous solution, comprising contacting the aqueous solution with a compound comprising one or more carbonyl moieties having an equilibrium constant for a hydration of the carbonyl moiety of at least about 0.5; separating a composition comprising the hydrated compound from the aqueous solution; and reacting the hydrated compound to obtain water.

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a Br?nsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

Domino C-F Bond Activation of the CF3 Group: Synthesis of Fluorinated Dibenzo[a,c][7]annulenes from 2-(Trifluoromethyl)-1-alkenes and 2,2′-Diceriobiaryls

The construction of ring-fluorinated seven-membered carbocycles was readily achieved via the domino SN2′-type/SNV reaction between 2-(trifluoromethyl)-1-alkenes and 1,4-carbodianions. The SN2′-type reaction of 2-(trifluoromethyl)-1-alkenes with 2,2′-diceriobiaryls generated the intermediary 1,1-difluoro-1-alkenes bearing a monoceriobiaryl moiety, which in turn underwent intramolecular SNV reaction to afford fluorinated 5H-dibenzo[a,c][7]annulenes.

Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via CuI-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-CF3-β,β-Disubstituted Nitroalkenes

A direct and convenient method has been developed for the synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C-3 position of the pyrrolidine ring. The synthesis system, CuI/Si-FOXAP-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides with β-CF3-β,β-disubstituted nitroalkenes, provides pyrrolidines with high diastereoselectivities (up to >98:2 d.r.) and excellent enantioselectivities (up to >99.9 ee) and performs well for a broad scope of substrates under mild conditions.

In Situ Proteome Profiling and Bioimaging Applications of Small-Molecule Affinity-Based Probes Derived from DOT1L Inhibitors

DOT1L is the sole protein methyltransferase that methylates histone H3 on lysine 79 (H3K79), and is a promising drug target against cancers. Small-molecule inhibitors of DOT1L such as FED1 are potential anti-cancer agents and useful tools to investigate the biological roles of DOT1L in human diseases. FED1 showed excellent in vitro inhibitory activity against DOT1L, but its cellular effect was relatively poor. In this study, we designed and synthesized photo-reactive and "clickable" affinity-based probes (AfBPs), P1 and P2, which were cell-permeable and structural mimics of FED1. The binding and inhibitory effects of these two probes against DOT1L protein were extensively investigated in vitro and in live mammalian cells (in situ). The cellular uptake and sub-cellular localization properties of the probes were subsequently studied in live-cell imaging experiments, and our results revealed that, whereas both P1 and P2 readily entered mammalian cells, most of them were not able to reach the cell nucleus where functional DOT1L resides. This offers a plausible explanation for the poor cellular activity of FED1. Finally with P1/P2, large-scale cell-based proteome profiling, followed by quantitative LC-MS/MS, was carried out to identify potential cellular off-targets of FED1. Amongst the more than 100 candidate off-targets identified, NOP2 (a putative ribosomal RNA methyltransferase) was further confirmed to be likely a genuine off-target of FED1 by preliminary validation experiments including pull-down/Western blotting (PD/WB) and cellular thermal shift assay (CETSA). Minimalist "clickable" probes: Small-molecule probes P1 and P2 based on FED1 (a known DOT1L inhibitor) were developed and successfully used in experiments including live-cell imaging, in situ proteome profiling, and off-target identification (see scheme).

Copper-Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate

A copper-mediated trifluoroacetylation of various arenediazonium salts with ethyl trifluoropyruvate is reported. The reaction proceeded smoothly under mild conditions at room temperature giving trifluoromethyl aryl ketones in moderate to good yields. A variety of functional groups, including methoxy, hydroxy, ester, ketone, trifluoromethyl, and halide groups, were well tolerated. A possible reaction mechanism involving an aryl radical intermediate was proposed and supported by experimental evidence. This reaction provides a new route to trifluoromethyl aryl ketones, notable synthetic targets, from the corresponding anilines.

Palladium-catalyzed carbonylative coupling of aryl iodides with an organocopper reagent: A straightforward procedure for the synthesis of aryl trifluoromethyl ketones

A palladium-catalyzed carbonylative coupling of aryl iodides with a (trifluoromethyl)copper reagent has been developed. A wide range of substrates have been transformed into their corresponding trifluoromethyl ketones in good to excellent yields under mild conditions with high efficiency and excellent functional-group compatibility. Preliminary mechanistic investigations suggest that the transmetallation of an acylpalladium intermediate with the (trifluoromethyl)copper reagent seems to be involved in the catalytic cycle. Notably, this report represents one of the few studies on carbonylative coupling with organocopper reagents.

PROCESS FOR THE PREPARATION OF HALO-SUBSTITUTED TRIFLUOROACETOPHENONES

The invention relates to a process for the preparation of a compound of formula I (I), wherein R1 is hydrogen, fluoro or chloro; which process comprises a) reacting a compound of formula II (II), wherein R1 is hydrogen, fluoro or chloro; with a nitration agent to the compound of formula (III), wherein R1 is hydrogen, fluoro or chloro; and b) reacting the compound of formula III with chlorine gas at temperature from 180°C to 250°C to the compound of formula I.

PROCESS FOR THE PREPARATION OF HALO-SUBSTITUTED BENZENES

The present invention relates to a process for the preparation of a compound of formula (I), wherein R1 is hydrogen, fluoro or chloro; which process comprises a) reacting a compound of formula (II), wherein R1 is hydrogen, fluoro or chloro; with a nitration agent to the compound of formula (III), wherein R1 is hydrogen, fluoro or chloro; b) reacting the compound of formula III with a chlorinating agent to the compound of formula (IV), wherein R1 is hydrogen, fluoro or chloro; and c) reacting the compound of formula (III) with chlorine gas at a temperature from 180°C to 250°C to the compound of formula (I).