7387-69-1

Basic information

• Product Name: N-BENZYL-2,2,2-TRIFLUORO-ACETAMIDE
• Synonyms: N-BENZYL-2,2,2-TRIFLUORO-ACETAMIDE;2,2,2-Trifluoro-N-(phenylmethyl)acetamide;Acetamide, 2,2,2-trifluoro-N-(phenylmethyl)-;Acetamide, N-benzyl-2,2,2-trifluoro-;N-Benzyltrifluoroacetamide;Nsc24676
• CAS NO: 7387-69-1
• Molecular Formula: C₉H₈F₃NO
• Molecular Weight: 203.16
• Product Categories: Aromatics;Miscellaneous Reagents
• Mol File: 7387-69-1.mol
• Article Data: 45

Chemical Properties

• Melting Point: 70.0 to 74.0 °C
• Boiling Point: 276.4°C at 760 mmHg
• Flash Point: 120.9°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 0.00482mmHg at 25°C
• Refractive Index: 1.464
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-BENZYL-2,2,2-TRIFLUORO-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-2,2,2-TRIFLUORO-ACETAMIDE(7387-69-1)
• EPA Substance Registry System: N-BENZYL-2,2,2-TRIFLUORO-ACETAMIDE(7387-69-1)

Safety Data

• Hazardous Substances Data: 7387-69-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 1362, 1987 DOI: 10.1021/jo00383a042Tetrahedron Letters, 36, p. 7419, 1995 DOI: 10.1016/0040-4039(95)01557-4

InChI:InChI=1/C9H8F3NO/c10-9(11,12)8(14)13-6-7-4-2-1-3-5-7/h1-5H,6H2,(H,13,14)

Upstream product

• 455-46-9 2,4,6-trinitro-1,7-bis-trifluoroacetoxy-2,4,6-triaza-heptane 
• 100-46-9 benzylamine 
• 407-25-0 trifluoroacetic anhydride 
• 13089-11-7 methyl 3,3,3-trifluoropyruvate 
• 5672-89-9 N-trifluoroacetoxy succinimide 
• 103-67-3 benzyl-methyl-amine 
• 100-52-7 benzaldehyde 
• 76-05-1 trifluoroacetic acid 
• 383-63-1 ethyl trifluoroacetate, 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 367-64-6 n-butyl trifluoroacetate 
• 212615-81-1 2-hydroxy-5,5-pentamethylene-2-trifluoromethyltetrahydro-4-pyranone 
• 212615-80-0 2-hydroxy-5,5-dimethyl-2-(trifluoromethyl)tetrahydro-4H-pyranone 
• 1466-67-7 1,3-dibenzylurea 

Downstream Products

• 125080-71-9 2-Ethoxy-3-phenyl-5-(trifluoromethyl)-Δ⁴-1,4,2-oxazaphospholine 
• 14618-33-8 2,2,2-trifluoro-N,N-bis(phenylmethyl)acetamide 
• 189438-89-9 N-Benzyl-N-((Z)-but-2-enyl)-2,2,2-trifluoro-acetamide 
• 439930-58-2 (Me2Al[μ,η2-BnNC(O)CF3])2 
• 75-89-8 2,2,2-trifluoroethanol 
• 100-46-9 benzylamine 
• 347195-55-5 (R)-1-benzyl-3-ethylpiperazine 
• 674283-98-8 piperazinone 
• 68464-36-8 N-benzyl-2,2,2,-trifluoro-N-methylacetamide 
• 148943-71-9 N-Benzyl-N-((E)-but-2-enyl)-2,2,2-trifluoro-acetamide 
• 622-78-6 Benzyl isothiocyanate 
• 119874-75-8 2-<2-(N-benzyltrifluoroacetamido)ethyl>-1,3-dioxolane 

Relevant articles and documents

Direct palladium-catalyzed ortho-arylation of benzylamines

Unsubstituted benzylamines and N-methylbenzylamine can be ortho-arylated under palladium catalysis at 130 °C. The reactions require the presence of trifluoroacetic acid and silver acetate.

A CO2-Catalyzed Transamidation Reaction

Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular,N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO2-catalyzed transamidation versus a N2atmosphere. Comparative Hammett studies and kinetic analysis were conducted to elucidate the catalytic activation mechanism of molecular CO2, which was supported by DFT calculations. We attributed the positive effect of CO2in the transamidation reaction to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO2

Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines

Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.