Ethyl 3-amino-4,4,4-trifluorocrotonate Chemical Properties

Melting point:

26°C

Boiling point:

83 °C15 mm Hg(lit.)

Density 

1.245 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.424(lit.)

Flash point:

149 °F

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Colourless to Pale Yellow Low-Melting to Semi-Solid

pka

0.76±0.70(Predicted)

color 

White or Colorless to Light yellow

FreezingPoint 

22.0 to 26.0 ℃

Sensitive 

Air Sensitive

BRN 

4397839

InChIKey

NXVKRKUGIINGHD-ONEGZZNKSA-N

CAS DataBase Reference

372-29-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T,Xi

Risk Statements 

20/21/22-36/37

Safety Statements 

26-36-36/37

RIDADR 

3259

WGK Germany 

3

Hazard Note 

Toxic/Irritant

HazardClass 

IRRITANT

HazardClass 

8

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ethyl 3-amino-4,4,4-trifluorocrotonate Usage And Synthesis

Chemical Properties

Colourless liquid or white solid

Uses

Ethyl 3-amino-4,4,4-trifluorocrotonate is used as building block in chemical synthesis. Attributes Development Product Contact

Synthesis

A slurry of sodium enolides was prepared from ethyl trifluoroacetate (88.1 g, 1.0 mol) and ethyl acetate (71.05 g, 0.50 mol) by mixing with solid sodium ethoxide (34.05 g, 0.5 mol). The mixture was evaporated and concentrated with reference to the operation of Example 1. Subsequently, 250 ml of cyclohexane was added to the reaction system, followed by ammonium acetate (77.1 g, 1.0 mol) and anhydrous acetic acid (39.0 g, 0.65 mol). The resulting suspension was heated to boiling, water was separated by distillation and cyclohexane was refluxed into the reaction mixture. The reaction was terminated after 5 hours. The organic phase was separated by adding 300 mL of water. Cyclohexane was removed from the organic phase by distillation and the product was subsequently fractionated under vacuum. 57.0 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate was obtained with 97.4% purity and 62% yield. The product was analyzed by EI mass spectrometry ([M+] = 183 AMU), 1H-NMR (7.6 ppm, NH; 4.86 ppm, 1H, CH; 4.08 ppm, Quadruple peak, 2H, ethyl; 1.18 ppm, Triple peak, 3H, ethyl) and 13C-NMR (168 ppm, COOEt; 147 ppm, Quadruple peak, C-NH2. 120 ppm, broad quadruple peak, CF3; 82 ppm, quadruple peak, CH; 59 ppm, ethyl; 14 ppm, ethyl) were characterized.

References

[1] Patent: WO2004/16579, 2004, A1. Location in patent: Page 9; 10

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