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354-38-1 - 2,2,2-Trifluoroacetamide, 97% - A14451 - Alfa Aesar

A14451 2,2,2-Trifluoroacetamide, 97%

CAS Number
354-38-1
Synonyms

Size Price ($) Quantity Availability
25g 35.37
100g 100.04
500g 284.61
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2,2,2-Trifluoroacetamide, 97%

MDL
MFCD00008008
EINECS
206-559-9

Chemical Properties

Formula
CF3CONH2
Formula Weight
113.04
Melting point
70-75°
Boiling Point
162-164°
Solubility
Soluble in water (460 g/L at 20°C), alcohol, ether, chloroform (partially), and methanol.

Applications

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.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents, strong acids, strong bases and strong reducing agents.

Literature References

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):

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1753625
Harmonized Tariff Code
2924.19
TSCA
Yes

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