58808-61-0

Usage

Uses

Used in Chemical Synthesis:
Ethanone, 2,2,2-trifluoro-1-(4-nitrophenyl)(9CI) is used as a reagent in organic synthesis for the preparation of various chemical compounds. Its unique structure allows for versatile reactions and transformations, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
Ethanone, 2,2,2-trifluoro-1-(4-nitrophenyl)(9CI) is used as a building block for the preparation of various pharmaceutical compounds. Its potential biological and pharmacological activities make it a promising candidate for the development of new drugs with therapeutic applications.
Used in Drug Discovery and Development:
Ethanone, 2,2,2-trifluoro-1-(4-nitrophenyl)(9CI) is a subject of research in drug discovery and development due to its potential biological and pharmacological properties. Its unique structure and reactivity make it a valuable tool for exploring new therapeutic targets and developing innovative drug candidates.

Upstream product

• 110-86-1 pyridine 
• 122-04-3 4-nitro-benzoyl chloride 
• 98-88-4 benzoyl chloride 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 144459-68-7 α,α-bis(trifluoromethyl)-4-nitrobenzylalkohol 
• 241127-76-4 2,2,2-trifluoro-1-(4-nitrophenyl)ethan-1-ol 
• 555-16-8 4-nitrobenzaldehdye 
• 181820-18-8 S-(tert-butyl)trifluorothioacetate 
• 24067-17-2 4-nitrophenylboronic acid 
• 62-23-7 4-nitro-benzoic acid 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 97800-77-6 N,N-Dimethylvalin-(p-nitrophenyl)ester 
• 144459-68-7 α,α-bis(trifluoromethyl)-4-nitrobenzylalkohol 
• 144459-56-3 4-nitrobenzoesaeure-α,α-bis(trifluormethyl)-4-nitrobenzylester 
• 1617507-18-2 (S)-12-(4-nitrophenyl)-12-trifluoromethyl-5,6,11,12-tetrahydrobenzo[2,3]azepino[5,6-b]indole 
• 60979-14-8 1-nitro-4-(1,1,2,2,2-pentafluoroethyl)-benzene 

Relevant academic research and scientific papers

Trifluoromethylation of Benzoic Acids: An Access to Aryl Trifluoromethyl Ketones

The trifluoromethylation of benzoic acids with TMSCF3 was achieved through nucleophilic substitution with the use of anhydrides as an in situ activating reagent. Under the reaction conditions, a wide range of carboxylic acids including the bioactive ones worked well, thus providing a facile and efficient method for preparing aryl trifluoromethyl ketones from the readily available starting materials.

Palladium-catalyzed fluoroacylation of (Hetero)arylboronic acid with fluorothioacetates at ambient temperature

A palladium-catalyzed fluoroacylation of (hetero)aryl boronic acid with the fluorothioacetates is described at ambient temperature. A variety of aryl, and heteroaryl boronic acids are compatible in the reaction, affording the corresponding fluoroalkyl ketones in moderate to good yields. Further late-stage di-, and trifluoroacylation of drug molecule clofibrate and estrone demonstrated the synthetic practicability of this protocol.2009 Elsevier Ltd. All rights reserved.

Oxidation of α-trifluoromethyl and non-fluorinated alcohols: Via the merger of oxoammonium cations and photoredox catalysis

We present an alcohol oxidation strategy to access α-trifluoromethyl ketones (TFMKs) merging catalytic oxoammonium cation oxidation with visible-light photoredox catalysis. This work uses 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl as an organic oxidant capable of generating TFMKs in good yields. The methodology serves as an improvement over previous reports of an analogous oxidation strategy requiring superstoichiometric quantities of oxidant. Both primary and secondary non-fluorinated alcohols can also be oxidised in good yields.

Enantioselective Synthesis of Trifluoromethyl α,β-Unsaturated δ-Lactones via Vinylogous Aldol-Lactonization Cascade

The novel vinylogous aldol-lactonization cascade of alkylidene oxindole with trifluoromethyl ketones is presented. The reaction, catalyzed by a bifunctional tertiary amine, provides an efficient application of the vinylogous reactivity of alkylidene oxindoles for the preparation of enantioenriched trifluoromethylated α,β-unsaturated δ-lactones.

Organocatalytic Aerobic Oxidation of α-Fluoroalkyl Alcohols to Fluoroalkyl Ketones at Room Temperature

The organocatalytic aerobic oxidation of electron-deficient α-fluoroalkyl alcohols at room temperature is described. The resulting fluoroalkyl ketones are versatile synthetic intermediates for a variety of fluorine-containing molecules. This otherwise difficult transformation has now been accomplished by the reaction of α-fluoroalkyl alcohols with N-oxyl radicals, catalytically generated from 9-azabicyclo[3.3.1]nonan-3-one N-oxyl/nitrogen oxide (keto-ABNO/NOx) and oxygen in acetic acid (AcOH), affording the corresponding fluoroalkyl ketones in high yield. This operationally simple reaction can be performed under mild conditions, and was applied to a wide range of alcohols (20 examples), thus demonstrating a high functional group tolerance. Moreover, a modified one-pot protocol based on this method was able to convert an aldehyde to a trifluoromethyl ketone on a gram scale.

Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(Diazo-2,2,2-trifluoroethyl)arenes

Arenes substituted with perfluoroalkyl groups are attractive targets for drug and agrochemical development. Exploiting the carbenic character of donor/acceptor diazo compounds, a diversity-oriented synthesis of perfluoroalkylated arenes, for late stage fluorofunctionalization, is described. The reaction of 1-(diazo-2,2,2-trifluoroethyl)arenes with HF, F/Br, F2, CF3H, and CF3SH sources give direct access to a variety of perfluoroalkyl-substituted arenes presenting with incremental fluorine content. The value of this approach is also demonstrated for radiochemistry and positron emission tomography with the [18F]-labeling of CF3CHF-, CF3CBrF-, and CF3CF2-arenes from [18F]fluoride.

Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX)

A two-step process for the synthesis of aryl and heteroaryl trifluoromethyl ketones from the corresponding aldehydes is described. Trifluoromethyl alcohols were prepared from aryl and heteroaryl aldehydes in excellent yields using catalytic amount of K2CO3. The trifluoromethyl alcohols were then oxidized conveniently and efficiently by o-iodoxybenzoic acid (IBX) under mild conditions to get the desired functionalized aryl and heteroaryl trifluoromethyl ketones.

Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt

A simple, mild method for the oxidation of α-trifluoromethyl alcohols to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2,2,6,6-tetramethyl-1- piperidinyloxy (1c), is easily recovered and can be conveniently reoxidized to regenerate the oxoammonium salt.

A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation

Oxidation of various fluoroalkyl-substituted methanol derivatives under the influence of a catalytic amount of sodium 2-iodobenzenesulfonate and Oxone in CH3CN or CH3NO2 was investigated in detail. The efficiency of the newly developed oxidation was also evaluated by comparison to other oxidations, such as Dess-Martin, PDC, and Swern oxidation.

Silver compounds in synthetic chemistry. Part 5: Selective syntheses of trifluoromethylketones, RCOCF3, from trifluoromethylsilver, AgCF3, and corresponding acyl chlorides, RCOCl

Trifluoromethylketones of aromatics, heteroaromatics and olefins are formed selectively from reactions of trifluoromethylsilver and the corresponding carboxylic acid chlorides in moderate to excellent yields. The conditions chosen are dependent on the nature of the acyl chloride. Attempts to prepare alkyl(trifluoromethyl)ketones yielded product mixtures of the corresponding acyl fluorides, trifluoromethyl-, pentafluoroethyl- and n-heptafluoropropyl ketones.