361-11-5

Basic information

• Product Name: N-trifluoroacetyl acetanilide
• Synonyms: N-trifluoroacetyl acetanilide
• CAS NO: 361-11-5
• Molecular Weight: 231.174
• Mol File: 361-11-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-trifluoroacetyl acetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: N-trifluoroacetyl acetanilide(361-11-5)
• EPA Substance Registry System: N-trifluoroacetyl acetanilide(361-11-5)

Safety Data

• Hazardous Substances Data: 361-11-5(Hazardous Substances Data)

Upstream product

• 103-84-4 Acetanilid 
• 407-25-0 trifluoroacetic anhydride 
• 613-91-2 acetophenone oxime 

Downstream Products

• 328-11-0 trifluoro-acetic acid-(2,5-dichloro-anilide) 
• 103-84-4 Acetanilid 

Relevant articles and documents

Beckmann rearrangement of acetophenone oximes to the corresponding amides organo-catalyzed by trifluoroacetic acid for sustainable NSAIDs synthesis

The Beckmann rearrangement of acetophenone oximes to the corresponding amides (4-hydroxyacetophenone oxime to N-acetyl-4-hydroxyacetanilide and acetophenone oxime to N-phenylacetamide) is investigated by using trifluoroacetic acid (TFA) as catalyst. The reaction occurs either in the presence or in the absence of a suitable solvent. High selectivity and practically quantitative yield to amide is achieved in both cases at TFA/substrate > 3. Both TFA and the solvent (whenever present) could be easily reused by distillation since no protonation of amides occurs. The reaction proceeds via a multistep reaction path and the role of TFA is related not only to its acidity but also mainly to its ability on forming reactive trifluoroacetylated intermediates. In particular, the highly reactive trifluoroacetylated amide is actually the effective catalyst. Finally, a likely reaction path is proposed.