3832-55-1

Basic information

• Product Name: 2'-(TRIFLUOROMETHOXY)ACETANILIDE
• Synonyms: N-[2-(TRIFLUOROMETHOXY)PHENYL]ACETAMIDE;N1-[2-(TRIFLUOROMETHOXY)PHENYL]ACETAMIDE;2'-(TRIFLUOROMETHOXY)ACETANILIDE;2-(TRIFLUOROMETHOXY)ACETANILIDE;2'-(Trifluoromethoxy)acetanilide 97%;2'-(Trifluoromethoxy)acetanilide97%
• CAS NO: 3832-55-1
• Molecular Formula: C₉H₈F₃NO₂
• Molecular Weight: 219.16
• Mol File: 3832-55-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 68 °C
• Boiling Point: 261.5 ºC at 760 mmHg
• Flash Point: 111.9 ºC
• Appearance: /
• Density: 1.345 g/cm³
• Vapor Pressure: 0.0115mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: 2'-(TRIFLUOROMETHOXY)ACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-(TRIFLUOROMETHOXY)ACETANILIDE(3832-55-1)
• EPA Substance Registry System: 2'-(TRIFLUOROMETHOXY)ACETANILIDE(3832-55-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 3832-55-1(Hazardous Substances Data)

Usage

General Description

2'-(Trifluoromethoxy)acetanilide is an organic compound structured with a trifluoromethoxy group attached to an acetanilide base. Acetanilides are a type of anilides, made by reacting an aniline with acetic acid. Trifluoromethoxy specifically is known for its electron-withdrawing effect, which can affect the compound's reactivity. It features carbon, hydrogen, nitrogen, oxygen, and fluorine atoms in its molecular structure. As a specialized chemical, it's likely used in various scientific research, particularly in the development or synthesis of other chemical compounds. However, details regarding its specific uses, physical properties, toxicity, and safety measures might not be readily available and would likely be found in specialized chemical databases or material safety data sheets.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.