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Usage

Uses

Used in Pharmaceutical Industry:
4-(2,2,2-Trifluoroethoxy)benzonitrile is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 4-(2,2,2-trifluoroethoxy)benzonitrile serves as an intermediate for the production of various agrochemicals, including pesticides and herbicides. Its properties enable the creation of effective and targeted agrochemicals for agricultural use.
Used in Specialty Chemicals Production:
4-(2,2,2-Trifluoroethoxy)benzonitrile is utilized as a building block in the production of liquid crystals and other specialty chemicals. Its unique structure and properties make it a valuable component in the development of advanced materials with specific applications.
Used in Organic Synthesis:
As a versatile building block in organic synthesis, 4-(2,2,2-trifluoroethoxy)benzonitrile is employed for the synthesis of a wide range of organic compounds. Its reactivity and stability under various conditions make it a preferred choice for chemists working on the development of new organic compounds with diverse applications.

InChI:InChI=1/C9H6F3NO/c10-9(11,12)6-14-8-3-1-7(5-13)2-4-8/h1-4H,6H2

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 75-89-8 2,2,2-trifluoroethanol 
• 420-87-1 sodium 2,2,2-trifluoroethanolate 
• 6574-99-8 3,4-dichloro-benzonitrile 
• 623-00-7 4-bromobenzenecarbonitrile 
• 36801-01-1 4-cyanobenzenethiol 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 126747-14-6 4-cyanophenylboronic acid 
• 1194-02-1 4-fluorobenzonitrile 
• 555-16-8 4-nitrobenzaldehdye 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 767-00-0 4-cyanophenol 
• 619-72-7 4-nitrobenzonitrile 
• 93624-58-9 3-chloro-4-2',2',2'-trifluoroethoxybenzonitrile 

Downstream Products

• 50778-60-4 4-(2',2',2'-Trifluoroethoxy)benzamide 
• 93624-58-9 3-chloro-4-2',2',2'-trifluoroethoxybenzonitrile 
• 220709-85-3 4-(2',2',2'-Trifluoroethoxy)benzoylthiosemicarbazide 
• 220709-84-2 4-(2',2',2'-Trifluoroethoxy)benzoylhydrazide 

Relevant academic research and scientific papers

Aryl Ether Syntheses via Aromatic Substitution Proceeding under Mild Conditions

In this study, mild conditions for aromatic substitutions during the syntheses of aryl ethers were developed. In the reaction conditions, the choices of solvent, base, and the sequence for the addition of the reagents proved important. A wide variety of alcohols were used directly as nucleophiles and smoothly reacted with aryl chlorides that possessed either a nitro or a cyano group at either the ortho- or para-position. Controlled experiments we performed suggested that the reaction underwent a charge-transfer process mediated by a combination of DMF and tert-BuOK.

Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage

Aryl-heteroatom bonds (C-Het) are almost ubiquitously present in chemical molecules. However, methods for diverse C-Het bond formations from a simple substrate are limited. Herein, we report a convenient and efficient C-S bond transformation of aryl sulfoniums to various C-Het bonds (C-O, C-S, C-Sn, C-Si, C-Se) in the absence of any transition-metal catalyst. These reactions proceeded in mild conditions with a wide substrate scope.

Practical heterogeneous photoredox/nickel dual catalysis for C-N and C-O coupling reactions

Efficient C-N and C-O coupling reactions of aryl halides with amines and alcohols have been developed by using the strategy of heterogeneous visible light photoredox and nickel dual catalysis. Obviously, the joint use of inexpensive and bench-stable CdS and nickel salts, together with mild reaction conditions, makes these two transformations attractive for the synthetic community. This heterogeneous dual catalysis system also proved to be successful in the ligand-free catalytic hydroxylation of aryl bromide with water as a nucleophile. The practicality of this protocol is further emphasized by the scaled-up reaction and the reusability of heterogeneous photocatalysts.

From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

We have developed a simple and direct method for the synthesis of aryl ethers by reacting alcohols/phenols (ROH) with aryl ammonium salts (ArNMe3+), which are readily prepared from anilines (ArNR′2, R′=H or Me). This reaction proceeds smoothly and rapidly (within a few hours) at room temperature in the presence of a commercially available base, such as KOtBu or KHMDS, and has a broad substrate scope with respect to both ROH and ArNR′2. It is scalable and compatible with a wide range of functional groups.

Palladium-Catalyzed 2,2,2-Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of a Trifluoro Analogue of Sildenafil

A simple and convenient method was developed for the introduction of a 2,2,2-trifluoroethoxy group to various aromatic and heteroaromatic systems. The novel process utilizes aromatic chlorides as substrates, and tetrakis(2,2,2-trifluoroethoxy) borate salt as an inexpensive and readily available fluoroalkoxy source in a palladium-catalyzed cross-coupling reaction. The power of the developed methodology was demonstrated in the synthesis of a fluorous derivative of Sildenafil.

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.

Well-defined copper(I) fluoroalkoxide complexes for trifluoroethoxylation of aryl and heteroaryl bromides

Copper(I) fluoroalkoxide complexes bearing dinitrogen ligands were synthesized and the structure and reactivity of the complexes toward trifluoroethoxylation, pentafluoropropoxylation, and tetrafluoropropoxylation of aryl and heteroaryl bromides were investigated. Efficiency drive: A series of copper(I) fluoroalkoxide complexes bearing N,N ligands have been prepared and structurally characterized. These well-defined complexes serve as efficient reagents for the fluoroalkoxylation of aryl and heteroaryl bromides to produce a wide range of trifluoroethyl, pentafluoropropyl, and tetrafluoropropyl (hetero)aryl ethers in good to excellent yields.

Transition-Metal-Mediated Synthesis of Trifluoroethyl Aryl Ethers

A series of well-defined copper(I) fluoroalkoxide complexes, [(phen)2Cu][OCH2RF], have been shown to undergo trifluoroethoxylation, pentafluoropropoxylation, and tetrafluoropropoxylation with aryl and heteroaryl bromides to generate the corresponding trifluoroethyl, pentafluoropropyl, and tetrafluoropropyl (hetero)aryl ethers in good to excellent yields. The reaction tolerates a variety of functional groups and demonstrates efficient scalability and practicality.