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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-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant