1682-66-2

Basic information

• Product Name: N-Ethyl-2,2,2-trifluoroacetamide
• Synonyms: N-Ethyl-2,2,2-trifluoroacetamide;AcetaMide, N-ethyl-2,2,2-trifluoro-
• CAS NO: 1682-66-2
• Molecular Formula: C₄H₆F₃NO
• Molecular Weight: 141.09
• Mol File: 1682-66-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 14-15 °C
• Boiling Point: 149.5°C at 760 mmHg
• Flash Point: 44.2°C
• Appearance: /
• Density: 1.207g/cm³
• Vapor Pressure: 4.01mmHg at 25°C
• Refractive Index: 1.342
• PKA: 11.55±0.46(Predicted)
• CAS DataBase Reference: N-Ethyl-2,2,2-trifluoroacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethyl-2,2,2-trifluoroacetamide(1682-66-2)
• EPA Substance Registry System: N-Ethyl-2,2,2-trifluoroacetamide(1682-66-2)

Safety Data

• Hazardous Substances Data: 1682-66-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H6F3NO/c1-2-8-3(9)4(5,6)7/h2H2,1H3,(H,8,9)

Upstream product

• 1740-99-4 O-(Trifluor-acetyl)-N,N-diaethyl-hydroxylamin 
• 109317-75-1 4-trifluoroacetyl-2,3-dihydrofuran 
• 75-04-7 ethylamine 
• 383-63-1 ethyl trifluoroacetate, 
• 557-66-4 ethanamine hydrochloride 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 1373763-28-0 2,2,2-trifluoro-N-(2-((2-(tritylamino)ethyl)amino)ethyl)-acetamide 

Relevant articles and documents

Sigmatropic isomerizations in azaallyl systems: XXII. 1,3-proton transfer in (N-alkyltrifluoroacetimidoyl)phosphonates

The reaction of N-alkyltrifluoroacetimidoyl chlorides with trialkyl phosphites leads to corresponding imidoylphosphonates CF 3C[P(O)(OAlk)2]=NCH2R. These compounds undergo irreversible 1,3-H shift catalyzed by nitrogenous bases to give phosphorylated imines CF3CH[P(O)(OAlk)2]N=CHR. The tendency for prototropism increases with increasing electronegativity of substituents R: CF3 > CH2OMe > H > Me. N-Cyclopentyl analogs of the obtained compounds show no tendency for prototropism. Imidoylphosphonates exist mainly as Z isomers [Z/E (6-10) : 1].

Convenient one-pot synthesis of N-substituted 3-trifluoroacetyl pyrroles

A new one-pot strategy for the synthesis of a series of new N-substituted 3-trifluoroacetyl pyrroles is presented. These compounds were obtained by the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with primary amines, which generated 1,1,1-trifluoro-3-(2-hydroxyethyl)-4-alkylaminobut-3-en-2-one intermediates. In most cases these intermediates were not stable enough to be isolated. Thus, in the same reaction vessel they were directly submitted to oxidation with PCC (Corey's reagent) to furnish 1,1,1-trifluoro-3-(2-ethanal)-4- alkylaminobut-3-en-2-ones, which under reflux underwent intramolecular cyclization to give the desired N-substituted 3-trifluoroacetyl pyrroles, in moderate yields. All of these pyrroles were tested against pan-susceptible Mycobacterium tuberculosis H37Rv and clinical isolates INH- and RMP-resistant strain and some of these compounds showed significant in vitro antimicrobial activity. Georg Thieme Verlag Stuttgart.

Conformations and Vibrational Dynamics of Six Monoalkyltrifluoroacetamides. Low-Resolution Microwave and Gas-Phase NMR Spectroscopic Studies

Low resolution microwave spectra of six N-alkyltrifluoroacetamides (F3C(O)NHR; r = CH3, C2H5, i-C3H7, n-C3H7, i-C4H9, t-C4H9) display band series consistent with a single species having the R group oriented syn to the carbonyl moiety. 5JH-F coupling constats observed in gas- and liquid-phase NMR spectra of N-methyltrifluoroacetamide confirm this assignment.For each molecule the observed rotational constats, anomalously broad microwave bandwidths, and absence of resolvable fine structure are consistent with predicted effects of rapid intramolecular vibrational redistribution (IVR).Sufficient state density for IVR in these molecules occurs at low internal energies.