87014-29-7

Usage

Uses

Used in Pharmaceutical Industry:
1-Nitro-3-(2,2,2-trifluoroethoxy)benzene is used as an intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into complex organic molecules.
Used in Agrochemical Industry:
1-Nitro-3-(2,2,2-trifluoroethoxy)benzene is used as an intermediate in the synthesis of agrochemicals for its potential to contribute to the development of effective crop protection agents.
Used in Organic Synthesis:
1-Nitro-3-(2,2,2-trifluoroethoxy)benzene is used as a building block in organic synthesis for its versatility in forming a variety of organic compounds.
Used in Research Laboratories:
1-Nitro-3-(2,2,2-trifluoroethoxy)benzene is used in research laboratories for its potential applications in the development of new chemical compounds and materials.
Used in Production of Dyes and Pigments:
1-Nitro-3-(2,2,2-trifluoroethoxy)benzene has potential applications in the production of dyes and pigments due to its chemical structure and properties.
Used in Electronic Materials:
1-Nitro-3-(2,2,2-trifluoroethoxy)benzene has potential applications in the production of electronic materials, possibly due to its unique properties and reactivity.
It is important to handle 1-Nitro-3-(2,2,2-trifluoroethoxy)benzene with care as it can be hazardous to health and the environment if not properly managed.

Upstream product

• 99-65-0 meta-dinitrobenzene 
• 420-87-1 sodium 2,2,2-trifluoroethanolate 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 75-89-8 2,2,2-trifluoroethanol 
• 586-36-7 3-nitrophenyldiazonium tetrafluoroborate 
• 13331-27-6 m-nitrobenzene boronic acid 
• 585-79-5 m-nitrobromobenzene 

Relevant academic research and scientific papers

Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling

Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst tBuBrettPhos Pd G3 and Cs2CO3 in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and-poor (hetero)arenes. The method provides access to 18F-labeled trifluoroethyl ethers by cross-coupling with [18F]trifluoroethanol.

Copper-catalyzed oxidative trifluoroethoxylation of aryl boronic acids with CF3CH2OH

A mild and efficient copper-catalyzed oxidative trifluoroethoxylation of aryl and heteroaryl boronic acids with CF3CH2OH has been developed. This protocol tolerates a range of functional groups, allowing access to a variety of aryl and heteroaryl trifluoroethyl ethers.

Method for preparing aryl trifluoroethoxyl ether

The invention relates to a method for preparing aryl trifluoroethoxyl ether. The method includes the steps that aryl boron compounds and trifluoroethanol are added to organic solvent, a copper salt catalyst, a ligand and an oxidizing agent are added, a reaction is conducted in a stirring mode for 1-40 hours at the temperature of 0-60 DEG C, filtering is conducted, column chromatography isolation is conducted, and the aryl trifluoroethoxyl ether is obtained. The method is simple in operation, raw materials are easy to obtain, the reaction condition is mild, the substrate universality is wide, the environmental friendliness is achieved, and the method is applicable to industrial application.

A fast radical chain mechanism in the polyfluoroalkoxylation of aromatics through NO2 group displacement. Mechanistic and theoretical studies

(Chemical Equation Presented) Introduction of polyfluoroalkoxy and polyfluoroalkylthio substituents in aromatic rings can be achieved with mild conditions and short times thorough reaction of concentrated solutions of dinitrobenzenes in DMF with polyfluoro alcohols and polyfluoro thiols in moderate excess, in the presence of excess tetrabutylammonium fluoride as a base. Mechanistic studies suggest that under these conditions a fast radical chain mechanism operates. This mechanism is elicited by oxidation of a Meisenheimer complex and proceeds through a radical aromatic substitution with the polyfluoroalkoxy or the polyfluoroalkylthio radicals as key intermediates. At low concentrations, entrainment can be achieved with superoxide anion. A rationale for this effect is discussed. Answers to particular questions about the proposed mechanism are achieved through a theoretical study at the B3LYP/6-31+G(d,p) level. Specifically, the competition between the radical mechanism and the corresponding polar one (classical SNAr reaction) is studied in that way, with the conclusion that the key steps of the radical mechanism in our reaction conditions (polar aprotic solvent) are at least as efficient as the ones of the polar one, thus justifying the observed kinetic advantage for the chain reaction in the conditions where an efficient initiation occurs.

A product analytical study of the thermal and photolytic decomposition of some arenediazonium salts in solution

Products of thermal and photochemical reactions of eleven arenediazonium tetrafluoroborates in various solvents have been analyzed. All compounds in most solvents undergo unimolecular heterolysis to give singlet aryl cations which are captured by solvent. This mechanism is dominant for arenediazonium ions without electron-withdrawing substituents in all solvents, and the only reaction observed in water. Additionally, appreciable yields of fluoroarenes are obtained by fluoride abstraction by the aryl cation from fluorinated solvents and from tetrafluoroborate in fluorinated solvents. Yields from photochemical processes are very similar to those from thermal reactions indicating that the main reactions proceed through common or very similar intermediates. Aryl cations formed from ion-paired diazonium ions may react with the counterion, but fragmentation of dissociated diazonium ions leads only to solvent-derived product. Some arenediazonium ions in some solvents undergo an alternative radical reaction leading principally to hydrodediazoniation. It is proposed that this reaction involves initial rate-limiting electron transfer from ethanol to the arenediazonium ion followed rapidly by homolysis of the resultant aryldiazenyl radical. Within the same solvent cage, the aryl radical then either abstracts an α-hydrogen from the ethanol radical cation generated in the first step to give the reduction product and protonated acetaldehyde, or combines with it at the oxygen to give a protonated aryl ethyl ether.

Dediazoniation reactions of arenediazonium ions under solvolytic conditions: Fluoride anion abstraction from trifluoroethanol and α-hydrogen atom abstraction from ethanol

Arenediazonium salts decompose thermally and photochemically in trifluoroethanol to yield trifluoroethyl ethers and (in part by fluoride abstraction from the solvent) fluoroarenes; the less reactive compounds in trifluoroethanol decompose readily in ethanol to give arenes in a radical reaction involving abstraction of the α-hydrogen from the ethanol.

Aromatic Fluoroalkoxylation via Direct Displacement of a Nitro or Fluoro Group

Nitro- and fluorobenzenes substituted with a range of electron-withdrawing groups readily undergo fluoroalkoxylation via direct displacement of the nitro or fluoro group.A number of compounds, which cannot be usefully prepared by direct displacement of a chloro group and which are otherwise inaccessible, have been synthesized.Yields and reaction conditions are comparable to those reported by other workers for reactions involving strong nucleophiles.

Aromatic Fluoroalkoxylation via Direct Aromatic Nucleophilic Substitution

The reaction of activated aryl and heteroaryl halides with fluorinated alkoxide anions is described.In all cases, substitution of the halogen by a fluoroalkoxy group was observed.The effect of solvent, time, temperature, the activating group, leaving group, and the nucleophile on this reaction is also discussed.