Trifluoroacetamide Chemical Properties

Melting point:

65-70 °C (lit.)

Boiling point:

162.5 °C (lit.)

Density 

1.4176 (estimate)

bulk density

960kg/m3

Flash point:

162-164°C

storage temp. 

Store below +30°C.

solubility 

460 g/L (20°C)

pka

12.33±0.50(Predicted)

form 

Crystalline Powder or Crystals

color 

White to pale yellow or beige

PH

3.6 (460g/l, H2O, 23℃)

Water Solubility 

460 g/L (20 ºC)

BRN 

1753625

InChIKey

NRKYWOKHZRQRJR-UHFFFAOYSA-N

LogP

0.725 at 23℃ and pH4.83

Dissociation constant

0 at 23℃

CAS DataBase Reference

354-38-1(CAS DataBase Reference)

NIST Chemistry Reference

Acetamide, 2,2,2-trifluoro-(354-38-1)

EPA Substance Registry System

Acetamide, 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 

T

HazardClass 

8

PackingGroup 

III

HS Code 

29241900

MSDS

• Language:English Provider:2,2,2-Trifluoroacetamide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Trifluoroacetamide Usage And Synthesis

Chemical Properties

white to pale yellow or beige crystalline powder

Uses

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.

Application

Trifluoroacetamide was used as probe for determination of membrane potential and extra/intracellular volume of erythrocytes by fluorine-19 NMR studies.

Preparation

One-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 Description

Trifluoroacetamide is a good quencher of tryptophan fluorescence.

Synthesis

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 the American Chemical Society, 1943, vol. 65, p. 1459
[4] Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258
[5] Bulletin de la Classe des Sciences, Academie Royale de Belgique, 1922, vol. <5>8, p. 346

Trifluoroacetamide(354-38-1)Related Product Information

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