144181-61-3

Basic information

• Product Name: Acetamide, 2,2,2-trifluoro-N-(2-hydroxy-5-methylphenyl)-
• CAS NO: 144181-61-3
• Molecular Formula: C9H8F3NO2
• Molecular Weight: 219.163
• Mol File: 144181-61-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Acetamide, 2,2,2-trifluoro-N-(2-hydroxy-5-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, 2,2,2-trifluoro-N-(2-hydroxy-5-methylphenyl)-(144181-61-3)
• EPA Substance Registry System: Acetamide, 2,2,2-trifluoro-N-(2-hydroxy-5-methylphenyl)-(144181-61-3)

Safety Data

• Hazardous Substances Data: 144181-61-3(Hazardous Substances Data)

Upstream product

• 19056-83-8 diethyl 2-{[(3-methylphenyl)amino]methylene}propane-1,3-dioate 
• 76-05-1 trifluoroacetic acid 
• 452-84-6 3-amino-4-fluorotoluene 
• 108-44-1 1-amino-3-methylbenzene 
• 65440-81-5 O-(4-methylphenyl)hydroxylamine 
• 407-25-0 trifluoroacetic anhydride 
• 95-84-1 3-amino-4-hydroxytoluene 

Downstream Products

• 227795-98-4 7,16-bis(2-hydroxy-5-methyl-3-trifluoroacetamidobenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 

Relevant articles and documents

Direct C-N bond cleavage of N-vinyl or N-allyl arylamines: A metal-free strategy for N-devinylation and N-deallylation

A simple and convenient N-devinylation and N-deallylation strategy for N-vinyl and N-allyl arylamines in the presence of TFA/oxone is presented with the formation of selective ortho-hydroxylated and N-trifluoroacylated arylamine product in good yields. Th

C-H oxygenation and N-trifluoroacylation of arylamines under metal-free conditions: A convenient approach to 2-aminophenols and N-trifluoroacyl-ortho- aminophenols

Direct ortho-hydroxylation through C-H oxygenation and N-trifluoroacylation of anilines was achieved in a single step under metal-free conditions by using a combination of TFA and oxone. The method allowed the formation of functionalised amino phenolic compounds such as ortho-hydroxy-N- trifluoroacetanilides in good yields with broad substrate scope.

Acid-catalyzed amino-migration of O-phenylhydroxylamines

The mechanism of amino-migration of O-phenylhydroxylamine (1a) was studied. It was found that 1 rearranges to give 2-aminophenol (50%) and 4-aminophenol (7%) in trifluoroacetic acid (TFA). The predominance of the ortho rearrangement of 1 clearly distinguishes this process from the Bamberger rearrangement. From cross-coupling experiments employing stable isotopes, it was clarified that the ortho rearrangement proceeds intramolecularly and the para rearrangement involves both intra- and intermolecular processes. Good first-order kinetics were obtained for the rearrangement. The Hammett plot (σ+) with a large negative slope (ρ = -7.8) indicates that initial heterolytic N-O bond cleavage of 1 occurs and generates a positive charge on the oxygen atom with considerable delocalization into the aromatic ring. An ion-molecule pair involving a phenoxenium ion and an ammonia molecule as an intermediate rationalizes all of the results. In this pair, intramolecular combination to the ortho position proceeds preferentially over that to the para position. Formation of catechol and hydroquinone can be explained in terms of nucleophilic attack of TFA on the phenoxenium ion in a solvent-separated pair.