1644-88-8

Usage

Uses

2-(Trifluoromethoxy)nitrobenzene is an impurity in the preparation of Riluzole (R510000).

InChI:InChI=1/C7H4F3NO3/c8-7(9,10)14-6-4-2-1-3-5(6)11(12)13/h1-4H

Upstream product

• 456-55-3 1-trifluoromethoxybenzene 
• 554-84-7 meta-nitrophenol 
• 7783-56-4 antimony(III) fluoride 
• 100-02-7 4-nitro-phenol 
• 98-95-3 nitrobenzene 
• 927-84-4 bis(trifluoromethyl)peroxide 
• 57830-55-4 2-((trifluoromethyl)sulfonyl)pyridine 
• 175676-65-0 2-trifluoromethoxyphenylboronic acid 

Downstream Products

• 1377582-60-9 3-thioureido-(4-trifluoromethoxy)benzenesulfonamide 
• 1377582-59-6 3-Isothiocyanato-4-trifluoromethoxy-benzenesulfonamide 
• 1261523-68-5 3-Amino-4-trifluoromethoxy-benzenesulfonamide 

Relevant academic research and scientific papers

Process Development and Scale-up of the Continuous Flow Nitration of Trifluoromethoxybenzene

In this work, continuous flow nitration of trifluoromethoxybenzene (TFMB) was conducted in a microchannel reactor. The effects of process parameters, including temperature, residence time, sulfuric acid strength, flow rate, and reactor structure, were systemically investigated. It was found that the aforementioned process parameters had significant effect on TFMB conversion, while the product selectivity was merely sensitive to the reaction temperature. On the basis of the results of process parameter optimization, a scale-up strategy combining microreactor with distributed packed tubular reactor was presented. Consequently, excellent performance was achieved in the combined reactor with a kilogram-scale production.

Method for synthesizing nitro (hetero) aromatic hydrocarbon

The invention discloses a method for synthesizing nitro (hetero) aromatic hydrocarbon, and belongs to the field of organic synthesis. According to the method, simple (hetero) aromatic hydrocarbon is taken as an initial raw material and is stirred and reacted in an organic solvent at 40-100 DEG C under the action of a nitration reagent, a lewis acid catalyst and protective gas, and nitro (hetero) aromatic hydrocarbon can be obtained. The method provided by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simple preparation process, good chemical selectivity, wide substrate application range, easy amplification and the like, has great application potential, and lays a good foundation for industrial production.

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen

Trifluoromethoxylated aromatics (ArOCF3) are valuable structural motifs in the area of drug discovery due to the enhancement of their desired physicochemical properties upon the introduction of the trifluoromethoxy group (CF3O). Although significant progress has been made recently in the introduction of CF3O group into aromatics, current methods either require the use of expensive trifluoromethoxylation reagents or require harsh reaction conditions. We present a conceptually new and operationally simple protocol for the direct C?H trifluoromethoxylation of (hetero)aromatics by the combination of the readily available trifluoromethylating reagent and oxygen under electrochemical reaction conditions. This reaction proceeds through the initial generation of CF3 radical followed by conversion to CF3O radical, addition to (hetero)aromatics and rearomatization. The utility of this electrochemical trifluoromethoxylation is illustrated by the direct incorporation of CF3O group into a variety of (hetero)aromatics as well as bio-relevant molecules.

Radical C?H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide

Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro- and medicinal chemistry. Radical C?H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large-scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which have been previously prepared via multi-step approaches.

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

The first example of photocatalytic trifluoromethoxylation of arenes and heteroarenes under continuous-flow conditions is described. Application of continuous-flow microreactor technology allowed to reduce the residence time up to 16 times in comparison t

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N?O Bond Redox Fragmentation

A simple trifluoromethoxylation method enables non-directed functionalization of C?H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF3 radical mechanism mediated by a photoredox catalyst, which triggers an N?O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner.

Process for the preparation of aryl trifluoromethyl ethers

A novel method for the preparation of aryl trifluoromethyl ethers which comprises reacting a phenol, a perhalomethane, and an antimony pentahalide. For example, 4-nitrophenol may be reacted with an excess over stoichiometry of both carbon tetrachloride and antimony trifluoride with a catalytic amount of antimony pentachloride to form 4-nitrophenyl trifluoromethyl ether.