400-59-9

Basic information

• Product Name: N-Butyltrifluoroacetamide
• Synonyms: N-Butyltrifluoroacetamide
• CAS NO: 400-59-9
• Molecular Formula: C₆H₁₀F₃NO
• Molecular Weight: 169.1449
• Mol File: 400-59-9.mol

Chemical Properties

• Boiling Point: 178.9°Cat760mmHg
• Flash Point: 62°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 0.966mmHg at 25°C
• Refractive Index: 1.37
• CAS DataBase Reference: N-Butyltrifluoroacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Butyltrifluoroacetamide(400-59-9)
• EPA Substance Registry System: N-Butyltrifluoroacetamide(400-59-9)

Safety Data

• Hazardous Substances Data: 400-59-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H10F3NO/c1-2-3-4-10-5(11)6(7,8)9/h2-4H2,1H3,(H,10,11)

Upstream product

• 109-73-9 N-butylamine 
• 407-25-0 trifluoroacetic anhydride 
• 383-63-1 ethyl trifluoroacetate, 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 1536-78-3 2-butyl trifluoroacetate 
• 354-38-1 2,2,2-trifluoroacetamide 

Downstream Products

• 313-32-6 N-trifluoroacetyl-di-n-butylamine 
• 592-82-5 butyl isothiocyanate 
• 5456-97-3 N-butyl-4-methylbenzamide 
• 14227-95-3 3-oxo-3-pyrrolidin-1-yl-propionitrile 

Relevant articles and documents

Efficient method for selective introduction of substituents as C(5) of isoleucine and other α-amino acids

A useful process for the position-selective remote bromination of N-trifluoroacetyl-α-amino esters is illustrated for the isoleucine case. The 5-bromoisoleucine derivative shown above can be used for the synthesis of many modified amino acids, as described herein.

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

Activation energies of aminolysis of aliphatic esters in aprotic media

Activation enthalpies and entropies for the third-order aminolysis reaction of n-butyl formate, n-butyl-trichloroacetate and sec-butyl trifluoroacetate were determined in solvents of various polarity and π-basicity. The importance of the steric requirements of the reagents together with high activation entropy values support the assumption of cyclic transition states for the reaction. Electrophilicity of the ester and the solvent properties predetermine the reaction mechanism in the range between the pathway through a zwitterionic intermediate for the formate and the nearly concerted reaction for the trichloroacetate. The negative activation energy of an aminolysis reaction should not necessarily be attributed to a good leaving group, but can be determined by the electrophilicity of the ester and the solvent effects.

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.

One-electron Oxidation of Closed-shell Molecules. Part 4. Acid-induced Oxidative Cleavage of Substituted 1,2,2,2-Tetraphenylethanones (Benzpinacolones) with Diaroyl Peroxides

The acid-induced oxidative cleavage of anispinacolone with diaroyl peroxides in 1,2-dichloroethane-trifluoroacetic acid (TFA) has been investigated.The principal two products after work-up are tris-(p-methoxyphenyl)methanol and p-methoxybenzoic acid; the latter was found as anhydrides in the reaction mixture.Free-radical formation in the course of the cleavage was verified by polymerization of added acrylonitrile in the oxidation by bis-(3,5-dinitrobenzoyl) peroxide.When the oxidation of anispinacolone (90percent (13)C) by dibenzoyl peroxide was carried out in a (13)C n.m.r. probe, an emission peak, assigned to p-methoxybenzoic trifluoroacetic anhydride, was observed.The logarithms of the rate constants for oxidation of p-substituted benzpinacolones by dibenzoyl peroxide were linearly correlated with the oxidation potentials of the benzpinacolones.These results are consistent with a single-electron transfer (s.e.t.) pathway from benzpinacolones to dibenzoyl peroxide.The oxidation is first-order in each reactant and is promoted by TFA.The effect of TFA is accounted for by two factors, (i) assisted O-O bond cleavage of the peroxide radical anion by TFA, and (ii) the formation of protonated peroxide, a more powerful oxidizing species.The former factor is dominant at lower TFA concentrations ( 0.05 M), the latter at higher concentrations.