3832-55-1

Usage

Uses

Used in Scientific Research:
2'-(TRIFLUOROMETHOXY)ACETANILIDE is used as a chemical intermediate for the synthesis of other chemical compounds, particularly in the field of organic chemistry. Its unique structure and reactivity, influenced by the electron-withdrawing trifluoromethoxy group, make it a valuable component in the development of new compounds with specific properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2'-(TRIFLUOROMETHOXY)ACETANILIDE may be used as a building block in the creation of new drug molecules. Its unique properties could contribute to the development of novel therapeutic agents with improved efficacy and selectivity.
Used in Chemical Synthesis:
2'-(TRIFLUOROMETHOXY)ACETANILIDE is used as a reagent in chemical synthesis processes, where its electron-withdrawing effect can influence the outcome of reactions, leading to the formation of desired products with specific characteristics.

InChI:InChI=1/C9H8F3NO2/c1-6(14)13-7-4-2-3-5-8(7)15-9(10,11)12/h2-5H,1H3,(H,13,14)

Upstream product

• 98-95-3 nitrobenzene 
• 1795-83-1 N-Phenylacetohydroxamic acid 
• 887144-94-7 Togni's reagent II 
• 100-65-2 N-Phenylhydroxylamine 
• 2314-97-8 iodotrifluoromethane 

Downstream Products

• 235101-48-1 2-nitro-6-(trifluoromethoxy)aniline 
• 235101-49-2 2-iodo-3-(trifluoromethoxy)nitrobenzene 
• 235101-50-5 2-iodo-3-(trifluoromethoxy)aniline 
• 131395-20-5 2-nitro-6-(trifluoromethoxy)acetanilide 

Relevant academic research and scientific papers

Selective C-O bond formation: Via a photocatalytic radical coupling strategy: Access to perfluoroalkoxylated (ORF) arenes and heteroarenes

Development of an efficient process that employs commercially available and cost effective reagents for the synthesis of perfluoroalkoxylated aromatic compounds (Ar-ORF) remains a daunting challenge in organic synthesis. Herein, we report the first catalytic protocol using readily available perfluoroalkyl iodides (RFI) and N-(hetero)aryl-N-hydroxylamides to access a wide range of perfluoroalkoxylated (hetero)arenes. Mild reaction conditions allow for selective O-RF bond formation over a broad substrate scope and are tolerant of a wide variety of functional groups. Mechanistic studies suggest the formation and recombination of persistent N-hydroxyl radicals and transient RF radicals under photocatalytic reaction conditions to generate N-ORF compounds that rearrange to afford the desired products.

TRIFLUOROMETHOXYLATION OF ARENES VIA INTRAMOLECULAR TRIFLUOROMETHOXY GROUP MIGRATION

The present invention provides a process of producing a trifluoromethoxylated aryl or trifluoromethoxylated heteroaryl having the structure: (I), wherein A is an aryl or heteroaryl, each with or without subsutitution; and R1 is -H, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), - (alkylaryl), - (alkylheteroaryl), -NH-(alkyl), -N(alkyl)2, -NH-(alkenyl), -NH-(alkynyl) -NH-(aryl), -NH-(heteroaryl), -O-(alkyl), -O-(alkenyl), -O-(alkynyl), -O-(aryl), -O-(heteroaryl), -S-(alkyl), -S- (alkenyl), -S-(alkynyl), -S-(aryl), or -S-(heteroaryl), comprising: (a) reacting a compound having the structure: (II), with a trifluoromethylating agent in the presence of a base in a first suitable solvent under conditions to produce a compound having the structure: (III); and (b) maintaining the compound produced in step (a) in a second suitable solvent under conditions sufficient to produce the trifluoromethoxylated aryl or trifluormethoxylated heteroaryl having the structure: (I).

Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration

The one-pot two-step intramolecular aryl and heteroaryl C-H trifluoromethoxylation recently reported by our group has provided a general, scalable, and operationally simple approach to access a wide range of unprecedented and valuable OCF3-containing building blocks. Herein we describe our investigations to elucidate its reaction mechanism. Experimental data indicate that the O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives is a radical process, whereas the OCF3-migration step proceeds via a heterolytic cleavage of the N-OCF3 bond followed by rapid recombination of a short-lived ion pair. Computational studies further support the proposed ion pair reaction pathway for the OCF3-migration process. We hope that the current study would provide useful insights for the development of new transformations using versatile N-(hetero)aryl-N-hydroxylamine synthons.

Trifluoromethoxylation of arenes: Synthesis of ortho- Trifluoromethoxylated aniline derivatives by OCF3 migration

Aryl trifluoromethoxylation by a two-step sequence of O-trifluoromethylation of N-aryl-N-hydroxylamine derivatives and intramolecular OCF3 migration is presented. This protocol allows easy access to a wide range of synthetically useful ortho-OCF3 aniline derivatives. In addition, it utilizes bench-stable reagents, is operationally simple, shows high functional-group tolerance, and is amenable to gram-scale as well as one-pot synthesis.Areaction mechanism of a heterolytic cleavage of the N-OCF3 bond followed by recombination of the resulting nitrenium ion and trifluoromethoxide is proposed for the OCF3-migration reaction.