114980-30-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,2,2-trifluoroethyl)-3-nitrobenzene is used as a key intermediate for the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(2,2,2-trifluoroethyl)-3-nitrobenzene is utilized as a building block for the creation of novel agrochemicals, such as pesticides and herbicides, that can improve agricultural productivity and crop protection.
Used in Dye and Pigment Production:
Due to its nitroaromatic properties, 1-(2,2,2-trifluoroethyl)-3-nitrobenzene is used as a starting material in the production of dyes and pigments, contributing to the vibrant colors and stability of these compounds in various applications.
Used in Industrial Chemicals:
1-(2,2,2-trifluoroethyl)-3-nitrobenzene also finds application in the production of other industrial chemicals, where its unique properties can be harnessed for specific technical requirements.
Safety Note:
It is important to handle 1-(2,2,2-trifluoroethyl)-3-nitrobenzene with caution due to its potential health hazards and environmental impact. Proper safety measures and disposal methods should be followed to minimize risks.

Upstream product

• 75-61-6 dibromodifluoromethane 
• 619-25-0 3-Nitrobenzyl alcohol 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 13331-27-6 m-nitrobenzene boronic acid 
• 129946-88-9 Umemoto's reagent 
• 887144-94-7 Togni's reagent II 
• 3718-22-7 3-nitrobenzaldehyde hydrazone 
• 373-88-6 2,2,2-trifluroethylamine hydrochloride 
• 99-61-6 3-nitro-benzaldehyde 
• 1877-73-2 3-nitro-benzeneacetic acid 
• 147531-11-1 trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt 
• 3958-57-4 1-bromomethyl-3-nitrobenzene 
• 645-00-1 m-iodonitrobenzene 
• 84750-94-7 1-(2,2-difluorovinyl)-3-nitrobenzene 

Relevant academic research and scientific papers

A facile synthesis of isomeric C -(2,2,2-trifluoroethyl)anilines

Three isomers of C-(2,2,2-trifluoroethyl)aniline were prepared on a multigram scale from readily available nitrophenylacetic acids in two steps. First, the carboxy groups of the latter were converted into the trifluoromethyl moieties by treatment with sul

Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2-Trifluoroethyl)arenes

Reacting hydrazones of arylaldehydes with Togni's CF3-benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this process include the easy access to hydrazone precursors on a large scale, speed and operational simplicity, and being transition metal-free.

Metal-Free Construction of the C(sp3)-CF3 Bond: Trifluoromethylation of Hydrazones with Togni's Reagent under Mild Conditions

A metal-free trifluoromethylation of hydrazones with Togni's reagent under mild conditions was developed. Various functional groups including ester, methoxy, dimethoxy, nitro, halogen, and heterocyclic compounds were tolerated. This simple and green strategy provides a practical tool to construct C(sp3)-CF3 bonds.

Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones

The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl β,β,β-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction sequences that consume excessive time, material, and labor resources while providing low yields of products. To complement these traditional strategies, we report a one-pot metal-free decarboxylative procedure for accessing β,β,β- trifluoroethylarenes and -heteroarenes from readily available ketones and aldehydes. This method features several benefits, including ease of operation, readily available reagents, mild reaction conditions, high functional-group compatibility, and scalability.

Switchable 2,2,2-trifluoroethylation and gem-difluorovinylation of organoboronic acids with 2,2,2-trifluorodiazoethane

The transition-metal-free 2,2,2-trifluoroethylation and gem-difluorovinylation of arylboronic acids were developed. By employing different reaction conditions, these transformations provide both (2,2,2-trifluoroethyl)arenes and gem-difluorovinylarenes fro

Copper-mediated deoxygenative trifluoromethylation of benzylic xanthates: Generation of a C-CF3 bond from an O-based electrophile

The conversion of an alcohol-based functional group, into a trifluoromethyl analogue is a desirable transformation. However, few methods are capable of converting O-based electrophiles into trifluoromethanes. The copper-mediated trifluoromethylation of benzylic xanthates using Umemoto's reagent as the source of CF3 to form C-CF3 bonds is described. The method is compatible with an array of benzylic xanthates bearing useful functional groups. A preliminary mechanistic investigation suggests that the C-CF3 bond forms by reaction of the substrate with in situ generated CuCF3 and CuOTf. Further evidence suggests that the reaction could proceed via a radical cation intermediate. Highly compatible and useful: The copper-mediated trifluoromethylation of benzylic xanthates using Umemoto's reagent as the source of CF3 to form C-CF3 bonds is described (see scheme). The method is compatible with an array of benzylic xanthates bearing useful functional groups. A preliminary mechanistic investigation suggests that the C-CF3 bond forms by reaction of the substrate with in situ generated CuCF3 and CuOTf. Copyright

Palladium-catalyzed 2,2,2-trifluoroethylation of organoboronic acids and esters

Trifluoroethylation: Aryl boronic acids can be catalytically trifluoroethylated with the readily available reagent CF3CH 2I (see scheme, dba=dibenzylideneacetone). The reaction tolerates a variety of functional groups and can be extended to the trifluoroethylation of aryl or alkenyl boronic esters. The method is also suitable for the late-stage installation of the CF3CH2 group into target molecules. Copyright

Cu-mediated chemoselective trifluoromethylation of benzyl bromides using shelf-stable electrophilic trifluoromethylating reagents

Copper-mediated chemoselective trifluoromethylation at the benzylic position by the use of shelf-stable electrophilic trifluoromethylating reagents 3 in good to high yields under mild conditions is described for the first time. The generality of this trifluoromethylation for a wide variety of benzyl bromides facilitates the rapid creation of structural diversity of medicinal candidates in drug discovery.

A New Route for the Preparation of Substituted 2,2-Difluorostyrenes and a Convenient Route to Substituted (2,2,2-Trifluoroethyl)benzenes

The (2,2-difluoroethenyl)zinc reagent II is coupled with aryl iodides or bromides in the presence of Pd(PPh3)4 in DMF to give the corresponding 2,2-difluorostyrenes IV. The 4-substituted (tetrafluoroaryl)copper reagents are coupled with 2,2-difluoro-1-iodoethylene (I) to produce the corresponding styrene derivatives VII. Both methods provide good yields of the coupled products. These products react with wet KF in DMF or DMSO to form the (2,2,2-trifluoroethyl)benzene derivatives VIII in good yields.

Novel Synthesis of 2,2,2-Trifluoroethyl Compounds from Homoallylic Alcohols: A Copper(I) Iodide-initiated Trifluoromethyl-Dehydroxylation Process

Benzyl, prop-2-enyl and allyl chlorodifluoroacetates 3a, bromodifluoroacetates 3b or fluorosulfonyldifluoroacetates 3c, when decomposed in the presence of 1 equivalent of copper(I) iodide at an appropriate temperature in dimethylformamide, gave the corresponding trifluoromethyl derivatives in good to excellent yields.The products can also be obtained directly by ester exchange of XCF2CO2Et (X = FSO2, Cl, Br) 6 and the corresponding alcohols in the presence of KF and CuI.A trifluoromethylation-dehydroxylation mechanism, initiated by CuI, is proposed.