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2,2,2-Trifluoroacetamide used in a convenient alternative to the Gabriel synthesis of primary amines from halides by N-alkylation followed by cleavage of the readily-hydrolyzed trifluoroacetyl group and for improved N-alkylation under phase-transfer conditions allowing successive alkylation with different alkyl groups.
Chuan-Zhou Tao.; Juan Li.; Yao Fu.; Lei Liu.; Qing-Xiang Guo. Copper-catalyzed synthesis of primary arylamines from aryl halides and 2,2,2-trifluoroacetamide. Tetrahedron Letters. 2008, 49 (1), 70-75.
Snefrid Gundersen.; Svein Samdal.; Ragnhild Seip.; Dmitry J. Shorokhov.; Tor G. Strand. Applequist. The molecular structure, conformation, potential to internal rotation and force field of 2,2,2-trifluoroacetamide as studied by gas electron diffraction and quantum chemical calculations. Journal of Molecular Structure. 1998, 445 (1-3), 229-242.
Has been used in a convenient alternative to the Gabriel synthesis of primary amines from halides by N-alkylation followed by cleavage of the readily-hydrolyzed trifluoroacetyl group: Synthesis, 941 (1984). For improved N-alkylation under phase-transfer conditions allowing successive alkylation with different alkyl groups, see: Synth. Commun., 18, 791 (1988). The method has been further extended by the use of ɑ-bromo esters to provide a high yielding route to ɑ-amino acids: J. Org. Chem., 56, 420 (1991):
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.