98651-71-9

Basic information

• Product Name: N-(2,4-Difluorophenyl)-trifluoroacetamide
• CAS NO: 98651-71-9
• Molecular Weight: 225.118
• Mol File: 98651-71-9.mol

Chemical Properties

• CAS DataBase Reference: N-(2,4-Difluorophenyl)-trifluoroacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,4-Difluorophenyl)-trifluoroacetamide(98651-71-9)
• EPA Substance Registry System: N-(2,4-Difluorophenyl)-trifluoroacetamide(98651-71-9)

Safety Data

• Hazardous Substances Data: 98651-71-9(Hazardous Substances Data)

Upstream product

• 367-25-9 2,4-difluorophenylamine 
• 407-25-0 trifluoroacetic anhydride 
• 83164-33-4 N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide 
• 404-24-0 2,2,2-trifluoro-N-phenylacetamide 

Relevant articles and documents

Fluorination of Aromatic Derivatives with Fluoroxytrifluoromethane and Bis(fluoroxy)difluoromethane

Fluoroxytrifluoromethane (CF3OF) and bis(fluoroxy)difluoromethane CF2(OF)2 are formed by the reaction of F2 with CO and CO2, respectively, over a CsF catalyst in a continouous-stream process.Both reagents react with aromatic substrates by an electrophilic substitution mechanism to yield fluoro-substituted derivatives.Fluorobenzene is produced in good yield from benzene, and aniline derivatives afford monofluorination products.Acetanilide (1), N-phenylmethanesulfonamide (2), α,α,α-trifluoroacetanilide (3), and 1,1,1-trifluoro(N-phenyl)methanesulfonamide (4) react with either reagent to yield mixtures of o- and p-fluoro-substituted derivatives.Solvent effects and competitive rate experiments demonstrate a preference for ortho substitution, especially in aprotic, nonpolar solvents.With particular substrates, these fluorinating agents are of practical synthetic utility, e.g., 2-fluoro-4-(trifluoromethyl)aniline is produced in high yield by fluorinating the intermediate 4-(trifluoromethyl)acetanilide (6) with CF3OF.Activated substrates such as toluene, xylenes, anisole, and cresols give mixtures of products which reduce the synthetic utility of these reagents.Nitrobenzene is fairly unreactive toward CF3OF and gives low yields of substitution products.

SELECTIVE CLEAVAGE OF THE ETHER AND AMIDE BONDS IN N-(2,4-DIFLUOROPHENYL)-2--3-PYRIDINECARBOXAMIDE (DIFLUFENICAN)

Heated to reflux in water containing 8 gpercent KOH, the herbicide diflufenican -3-pyridinecarboxamide, 1> was selectively transformed into 2--3-pyridinecarboxylic acid (2) plus 2,4-difluoroaniline (5); after 60 hr of heating, 27percent of the initial diflufenican was transformed, yielding 21percent (molepercent relative to initial diflufenican) of compound 2.Heated to reflux in a mixture of acetic acid + concentrate hydrochloric acid, diflufenican was transformed into a mixture of N-(2,4-difluorophenyl)-2-hydroxy-3-pyridinecarboxamide (3) and 2-hydroxy-3-carboxypyridine (4) plus 2,4-difluoroaniline (5) and 3-trifluoromethylphenol (6); after 48 hr of heating, diflufenican was completely transformed, yielding 28percent (molepercent relative to initial diflufenican) of compound 3, and 57percent of compound 4.The base catalyzed hydrolysis thus selectively yielded compound 2; the acid catalyzed one yielded compounds 3 + 4: diflufenican first was transformed into compound 3, which thereafter was transformed into compound 4.