340-11-4

Usage

Uses

Used in Pharmaceutical Industry:
2,2,2-Trifluoro-N,N-diphenylacetamide is utilized as a building block for the synthesis of various biologically active molecules and drugs. Its unique structure and properties contribute to the development of new pharmaceuticals, enhancing the therapeutic potential of existing medications.
Used in Agrochemical Production:
In the agrochemical industry, 2,2,2-trifluoro-N,N-diphenylacetamide serves as an intermediate in the production of various agrochemicals. Its role in this sector is crucial for the synthesis of compounds that protect crops and enhance agricultural productivity.
Used in Specialty Chemicals:
2,2,2-Trifluoro-N,N-diphenylacetamide is also employed in the production of specialty chemicals, where its specific properties are leveraged to create high-value products for niche applications in various industries. Its versatility in chemical reactions makes it an essential component in the synthesis of specialty chemicals.

Upstream product

• 100-65-2 N-Phenylhydroxylamine 
• 407-25-0 trifluoroacetic anhydride 
• 71-43-2 benzene 
• 122-39-4 diphenylamine 
• 383-63-1 ethyl trifluoroacetate, 
• 5856-89-3 lithium diphenylamide 
• 76-05-1 trifluoroacetic acid 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 96254-05-6 2-(trifluoroacetyloxy)pyridine 

Downstream Products

• 110972-14-0 N-(phenyl)-N-(2,2,2-trifluoroethyl)benzenamine 
• 157584-48-0 2,2,2-Trifluoro-N,N-diphenyl-thioacetamide 
• 75-89-8 2,2,2-trifluoroethanol 
• 122-39-4 diphenylamine 
• 128669-17-0 trans-1-Phenyl-4-(p-tolyl)-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline 
• 128644-90-6 1,4-Diphenyl-2-(trifluoromethyl)-1,2-dihydroquinoline 
• 110972-17-3 N-(1-Methoxy-2,2,2-trifluoroethyl)diphenylamine 

Relevant academic research and scientific papers

Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents

Lithium amides constitute one of the most commonly used classes of reagents in synthetic chemistry. However, despite having many applications, their use is handicapped by the requirement of low temperatures, in order to control their reactivity, as well as the need for dry organic solvents and protective inert atmosphere protocols to prevent their fast decomposition. Advancing the development of air- and moisture-compatible polar organometallic chemistry, the chemoselective and ultrafast amidation of esters mediated by lithium amides is reported. Establishing a novel sustainable access to carboxamides, this has been accomplished via direct C-O bond cleavage of a range of esters using glycerol or 2-MeTHF as a solvent, in air. High yields and good selectivity are observed while operating at ambient temperature, without the need for transition-metal mediation, and the protocol extends to transamidation processes. Pre-coordination of the organic substrate to the reactive lithium amide as a key step in the amidation processes has been assessed, enabling the structural elucidation of the coordination adduct [{Li(NPh2)(OCPh(NMe2))}2] (8) when toluene is employed as a solvent. No evidence for formation of a complex of this type has been found when using donor THF as a solvent. Structural and spectroscopic insights into the constitution of selected lithium amides in 2-MeTHF are provided that support the involvement of small kinetically activated aggregates that can react rapidly with the organic substrates, favouring the C-O bond cleavage/C-N bond formation processes over competing hydrolysis/degradation of the lithium amides by moisture or air.

Catalytic reduction of amides to amines by electrophilic phosphonium cations via FLP hydrosilylation

A catalytic methodology for the conversion of amides to amines is reported. Of the 25 examples described, 14 examples involve the reduction of N-trifluoroacetamides to the corresponding trifluoroethylamines. These reductions are achieved by catalytic hydrosilylation of the amide mediated by an electrophilic phosphonium cation (EPC) catalyst.

Trifluoroacetylation of amines with trifluoroacetic acid in the presence of trichloroacetonitrile and triphenylphosphine

We developed a mild and convenient trifluoroacetylation process for amines using a combination of trichloroacetonitrile and triphenylphosphine. The reaction that we designed is applicable to the trifluoroacetylation of a wide variety of amines, including amines with stereogenic centers, which underwent trifluoroacetylation without racemization.

A convenient synthesis of Trifluoroacetamides from sodium trifluoroacetate and amines

Trifluoroacetamides were prepared readily by reaction of sodium trifluoroacetate with triphenylphosphine di-iodide and amines consecutively under mild conditions with good yields.

N- and C-attacks on aromatics of phenylnitrenium ion generated from N-phenylhydroxylamine in the presence of trifluoroacetic acid containing polyphosphoric acid or trifluoroacetic anhydride

A phenylnitrenium ion formed from N-phenylhydroxylamine in the presence of trifluoroacetic acid (TFA) containing polyphosphoric acid (PPA) interacts with the counterion -O2CCF3 and the unshared electron-pair of H2O, showing Hammett's ρ values -5.2 and -4.0 for N- and C-attacks on aromatics PhX (X = H, Me, Et, Ph and Cl), respectively. The ratio N-/C-attack for this nitrenium ion is lower than for the nitrenium ion interacting with only the counterion; the latter nitrenium ion is generated by the use of trifluoroacetic anhydride (TFAA) instead of PPA or by reaction of phenyl azide with aromatics in TFA. The ratio for the former nitrenium ion is affected by the aromatic substituent X:X = Me > X = Et > X = Ph > X = H > X = OMe at 20 and 50°C. The order for X = Cl is between those of X = H and X = Ph at 20°C, but highest at 50°C. The ratio is increased by higher reaction temperature and by decreased concentration of TFA. The results are demonstrated from the mechanistic viewpoint for the nitrenium ions.

Microwave-promoted trifluoroacetylation of amines with TiO(CF3CO2)2

Conversion of amines to their corresponding trifluoroacetamides was performed with TiO(CF3CO2)2 in a conventional microwave oven under solvent-free conditions in excellent yields.

Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks

Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH2Rf (Rf = CF3, CHF2, CH2F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position α to the fluoromethyl (Rf) group, depending on the Rf and R groups.The effect of the Rf group on the promotion of the anodic α-methoxylation decreased in the order CF3, CHF2, and CH2F.This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the α-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines.The α-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds α to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods.

A convenient synthesis of perfluoroalkylated amines by oxidative desulfurization-fluorination

N-Perfluoroalkylamines were synthesized from perfluoroalkanethioamides, which were easily accessible from perfluoroalkanamides, by the action of N-halo imide and nBu4NH2F3.

2-(Trifluoroacetyloxy)pyridine as a Mild Trifluoroacetylating Reagent of Amines and Alcohols

A new trifluoroacetylating reagent, 2-(trifluoroacetyloxy)pyridine (TFAP), was prepared by the reaction of 2-pyridinol and trifluoroacetic anhydride.TFAP has been found to be effective in the trifluoroacetylation of aliphatic and aromatic amines and alcohols including phenol under mild conditions.The reaction of p-nitrophenol with TFAP in ether gave the hydrogen-bonded complex between the phenol and 2-pyridone.This reagent has also been shown to be useful for the intramolecular dehydration of aldehyde oximes and amides to give nitriles in high yields.

Electrolytic Transformation of Fluoroorganic Compounds. 3. Highly Regioselective Anodic Methoxylation of N-(2,2,2-trifluoroethyl)amines

Anodic methoxylation of N-alkyl-N-(2,2,2-trifluoroethyl)anilines and N-(2,2,2-trifluoroethyl)diphenylamine places the methoxy group in the α-position (toward the trifluoromethyl group); these products are useful building blocks for the construction of a c