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Trifluoroacetamide

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Trifluoroacetamide Basic information
Product Name:Trifluoroacetamide
Synonyms:Three fluoroacetaMide;TRIFLUOROACETAMIDE;TRIFLUOROACETIC ACID AMIDE;2,2,2-trifluoro-acetamid;Triflouroacetamide;TRIFLUOROACETAMIDE 98%;Acetamide, 2,2,2-trifluoro-;2,2,2-TRIFLOUROACETAMIDE
CAS:354-38-1
MF:C2H2F3NO
MW:113.04
EINECS:206-559-9
Product Categories:Amides;Carbonyl Compounds;Organic Building Blocks;top;bc0001
Mol File:354-38-1.mol
Trifluoroacetamide Structure
Trifluoroacetamide Chemical Properties
Melting point 65-70 °C (lit.)
Boiling point 162.5 °C (lit.)
bulk density960kg/m3
density 1.4176 (estimate)
Fp 162-164°C
storage temp. Store below +30°C.
solubility 460 g/L (20°C)
pka12.33±0.50(Predicted)
form Crystalline Powder or Crystals
color White to pale yellow or beige
PH3.6 (460g/l, H2O, 23℃)
Water Solubility 460 g/L (20 ºC)
BRN 1753625
InChI1S/C2H2F3NO/c3-2(4,5)1(6)7/h(H2,6,7)
InChIKeyNRKYWOKHZRQRJR-UHFFFAOYSA-N
SMILESNC(=O)C(F)(F)F
LogP0.725 at 23℃ and pH4.83
Dissociation constant0 at 23℃
CAS DataBase Reference354-38-1(CAS DataBase Reference)
NIST Chemistry ReferenceAcetamide, 2,2,2-trifluoro-(354-38-1)
EPA Substance Registry SystemAcetamide, 2,2,2-trifluoro- (354-38-1)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
RIDADR 1759
WGK Germany 3
Hazard Note Harmful/Irritant
TSCA TSCA listed
HazardClass 8
PackingGroup III
HS Code 29241900
Storage Class13 - Non Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
2,2,2-Trifluoroacetamide English
SigmaAldrich English
ACROS English
ALFA English
Trifluoroacetamide Usage And Synthesis
Chemical Propertieswhite to pale yellow or beige crystalline powder
Uses2,2,2-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.
ApplicationTrifluoroacetamide was used as probe for determination of membrane potential and extra/intracellular volume of erythrocytes by fluorine-19 NMR studies.
PreparationOne-pot synthetic approach to produce trifluoroacetamide has been developed using an electrochemical method with the B12 complex as a catalyst under mild conditions, in open air at room temperature. Thirty examples of trifluoroacetamide were synthesized from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) in moderate to good yields. This user-friendly strategy is compatible with a broad range of trifluoroacetamide syntheses.
10.1142/S1088424621500292
General DescriptionTrifluoroacetamide is a good quencher of tryptophan fluorescence.
Synthesis
Ethyl trifluoroacetate

383-63-1

Trifluoroacetamide

354-38-1

Example 5: Synthesis of the blocking isomer trifluoroacetamide 3a The block trans isomer 2a (0.93 g, 1.84 mmol, 503.4 g/mol) as a sulfate was dissolved in 15 mL of ethanol. Under argon protection, triethylamine (1.8 mL, 13 mmol) and ethyl trifluoroacetate (2.2 mL, 18 mmol) were slowly added (Figure 2a). The reaction mixture was stirred for 2.5 h at room temperature. Upon completion of the reaction, the volatiles were removed by distillation under reduced pressure. The resulting residue was dissolved in 300 mL of ethyl acetate and washed sequentially with 2 x 50 mL of 5% hydrochloric acid solution. The organic phase was dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford block-transfer isomerized trifluoroacetamide 3a as an orange solid (0.92 g, 100% yield, 501.4 g/mol). 1H NMR (methanol-d4) δ 8.35 (1H, d); 8.15 (1H, d); 7.80 (1H, s); 6.82 (1H, s); 6.65 (4H, m); 4.82 (2H, s).

References[1] Patent: US6448407, 2002, B1
[2] Journal of the American Chemical Society, 1943, vol. 65, p. 1459
[3] Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258
[4] Bulletin de la Classe des Sciences, Academie Royale de Belgique, 1922, vol. <5>8, p. 346
Tag:Trifluoroacetamide(354-38-1) Related Product Information
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