434-45-7

Usage

Uses

Used in Pharmaceutical Industry:
Trifluoroacetophenone is used as a neuroprotective agent for its ability to inhibit apoptosis in cerebellar granule neurons, offering potential benefits in the treatment of neurodegenerative disorders.
Used in Research Applications:
Trifluoroacetophenone is utilized as a research tool in the study of acetylcholinesterase inhibition and its effects on neuronal function, providing insights into the development of new therapeutic strategies for neurological conditions.

InChI:InChI=1/C8H11F3O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h6H,1-5H2

Upstream product

• 353-85-5 trifluoroacetonitrile 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 76-05-1 trifluoroacetic acid 
• 354-32-5 trifluoracetyl chloride 
• 71-43-2 benzene 
• 110-86-1 pyridine 
• 98-88-4 benzoyl chloride 
• 108-86-1 bromobenzene 
• 360-92-9 N,N-diethyl-2,2,2-trifluoroacetamide 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 106-37-6 1.4-dibromobenzene 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 309-10-4 1,1,1-trifluoro-2,2-dichloro-2-phenylethane 
• 321-31-3 1-(3-chlorophenyl)-2,2,2-trifluoroethanone 
• 340-06-7 S(+)-1-phenyl-2,2,2-trifluoroethanol 
• 340-04-5 1-phenyl-2,2,2-trifluoromethylethanol 
• 64361-93-9 (4,4-Dichloro-1-phenyl-1-trifluoromethyl-but-3-enyloxy)-trimethyl-silane 
• 56135-07-0 1,1,1-Trifluor-2-hydroxy-2-ethoxy-2-phenylethan 
• 1979-51-7 1,1,3,3,3-pentafluoro-2-phenylpropene 
• 70533-13-0 3,3,3-Trifluoro-2-phenyl-2-((trimethylsilyl)oxy)propanenitrile 
• 15256-70-9 (Z)-1-(1,1,1-trifluorohex-2-en-2-yl)benzene 
• 15256-81-2 (E)-1-(1,1,1-trifluorohex-2-en-2-yl)benzene 
• 3580-89-0 1,1,1-Trifluor-2-phenyl-2-hexen 
• 1716-77-4 3-Phenyl-3-hydroxy-3-(trifluoromethyl)propionic acid 
• 13006-19-4 α-(Chlordifluormethyl)-α-(trifluormethyl)-benzylalkohol 
• 19302-02-4 ((Z)-2-Chloro-2-fluoro-1-trifluoromethyl-vinyl)-benzene 

Relevant academic research and scientific papers

Ion-Molecule Reactions in Gaseous CF4/CO Mixtures. Formation and Reactivity of CF3CO(1+) Ions

The reactivity of CF3CO(1+) ions, formed via two different routes, has been studied in the gas phase by the joint use of mass spectrometric and radiolytic techniques, spanning a pressure range from 10-8 Torr to ca. 1 atm.The 23 kcal mol-1 exothermic addition of CF3(1+) to CO provides a route to CF3CO(1+) requiring third-body stabilization of the adduct ion.In the 10-8 Torr pressure regime of Fourier transform ion cyclotron resonance (FT-ICR) spectrometry, CF3CO(1+) ions from electron ionization (EI) induced fragmentation of trifluoroacetic anhydride yield NuCF3(1+) products from oxygen-centered nucleophiles (Nu) and XC6H4CO(1+) ions from aromatics (C6H5X).At ca. 1 atm trifluoroacetylated products are efficiently formed even with strongly deactivated aromatics, showing distinct intra- and intermolecular selectivity features pertaining to the reactant CF3CO(1+) ions.The reactivity pattern is interpreted according to a kinetic interplay of collisional and chemical events depending on the activation of C6H5X toward electrophilic attack.

UNUSUALLY LARGE KINETIC DEUTERIUM ISOTOPE EFFECTS ON OXIDATION REACTIONS. 1. THE MECHANISM OF HYDROXIDE-CATALYSED PERMANGANATE OXIDATION OF PhCD(CF3)OH AND PhCD(CH3)OH IN WATER

The oxidation of 1-phenyl-2,2,-trifluoroethanol (ROH) with potassium permanganate in 0.2 M aqueous sodium hydroxide solution at 25 deg C provides 2,2,2-trifluoroacetophenone as the sole product.The reaction rate constant, which was measured under pseudo-first order conditions by following the decrease in substrate concentration as a function of time, was found to be substantially smaller than previously reported.The primary kinetic deuterium isotope effect was measured as k2H/k2D= 14.7 +/- 1.0.A hydrogen-transfer mechanism involving significant tunnelling is proposed.The oxidation of 1-phenylethanol under similar reaction conditions yields acetophenone as the initial product.The kinetic deuterium isotope effect was found to be k2H/k2D = 5.2 +/- 0.8.

CARBON-14 KINETIC ISOTOPE EFFECTS AND MECHANISM IN THE SOLVOLYSIS OF 1,1,1-TRIFLUORO-2-PHENYL-2-PROPYL-3-14C p-TOLUENESULFONATE

In the solvolysis of 1,1,1-trifluoro-2-phenyl-2-propyl-3-14C p-toluenesulfonate there is only a small βC isotope effect, k/βk = 1.008+/-0.002.The result is as expected for a branching SN1/E1 reaction (mostly SN1).This is the first example of such a measurement.

Oxidation of fluoroalkyl alcohols using sodium hypochlorite pentahydrate [1]

Fluoroalkyl alcohols are effectivity oxidized to the corresponding fluoroalkyl carbonyl compounds by reaction with sodium hypochlorite pentahydrate in acetonitrile in the presence of acid and nitroxyl radical catalysts. Although the reaction proceeded slower under a nitroxyl radical catalyst- free condition, the desired carbonyl compounds were obtained in high yields. For the reaction with fluoroalkyl allylic alcohols, the corresponding α,β-epoxyketone hydrates were obtained in high yields.

Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis

This Article describes the development of a decarbonylative Pd-catalyzed aryl-fluoroalkyl bond-forming reaction that couples fluoroalkylcarboxylic acid-derived electrophiles [RFC(O)X] with aryl organometallics (Ar-M′). This reaction was optimized by interrogating the individual steps of the catalytic cycle (oxidative addition, carbonyl de-insertion, transmetalation, and reductive elimination) to identify a compatible pair of coupling partners and an appropriate Pd catalyst. These stoichiometric organometallic studies revealed several critical elements for reaction design. First, uncatalyzed background reactions between RFC(O)X and Ar-M′ can be avoided by using M′ = boronate ester. Second, carbonyl de-insertion and Ar-RF reductive elimination are the two slowest steps of the catalytic cycle when RF = CF3. Both steps are dramatically accelerated upon changing to RF = CHF2. Computational studies reveal that a favorable F2C-H - -X interaction contributes to accelerating carbonyl de-insertion in this system. Finally, transmetalation is slow with X = difluoroacetate but fast with X = F. Ultimately, these studies enabled the development of an (SPhos)Pd-catalyzed decarbonylative difluoromethylation of aryl neopentylglycol boronate esters with difluoroacetyl fluoride.

Decarboxylative and Deaminative Alkylation of Difluoroenoxysilanes via Photoredox Catalysis: A General Method for Site-Selective Synthesis of Difluoroalkylated Alkanes

A general method for site-selective difluoroalkylation of alkyl carboxylic redox esters with difluoroenoxysilanes through photoredox-catalyzed decarboxylative reaction has been developed. The reaction can also be extended to aliphatic amine derived pyridinium salts. This method has the advantages of high efficiency, mild reaction conditions, and broad substrate scope, including primary, secondary, and sterically hindered tertiaryl alkyl substrates, providing a general and practical route for applications in organic synthesis and pharmaceutical studies.

Catalytic Enantioselective Direct Aldol Addition of Aryl Ketones to α-Fluorinated Ketones

The catalytic enantioselective synthesis of α-fluorinated chiral tertiary alcohols from (hetero)aryl methyl ketones is described. The use of a bifunctional iminophosphorane (BIMP) superbase was found to facilitate direct aldol addition by providing the strong Br?nsted basicity required for rapid aryl enolate formation. The new synthetic protocol is easy to perform and tolerates a broad range of functionalities and heterocycles with high enantioselectivity (up to >99:1 e.r.). Multi-gram scalability has been demonstrated along with catalyst recovery and recycling. 1H NMR studies identified a 1400-fold rate enhancement under BIMP catalysis, compared to the prior state-of-the-art catalytic system. The utility of the aldol products has been highlighted with the synthesis of various enantioenriched building blocks and heterocycles, including 1,3-aminoalcohol, 1,3-diol, oxetane, and isoxazoline derivatives.

Novel Friedel-Crafts reaction method and catalyst thereof

The present invention relates to a novel method for preparing or synthesizing an acylated or alkylated aryl compound, such as acylated or alkylated benzene, through a reaction called Friedel-Crafts, and a novel catalyst for the method. The present invention particularly relates to a novel environment-friendly method for synthesizing the Friedel-Crafts reaction of the acylated or alkylated compound.

Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents

The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.

PROCESSES AND COMPOUNDS FOR THE DECARBOXYLATIVE AMINATION OF REDOX-ACTIVE ESTERS WITH DIAZIRINES

The invention described herein relates generally to processes for the synthesis of amine-containing organic compounds. More specifically, described herein relates to processes for the decarboxylative amination of redox-active esters with diazirines and the products formed thereof. Compounds for use in the above processes are also described.