Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate Chemical Properties

Boiling point:

80-82 °C1 mm Hg(lit.)

Density 

1.235 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.429(lit.)

Flash point:

220 °F

storage temp. 

2-8°C

form 

clear liquid

color 

Light orange to Yellow to Green

Specific Gravity

1.239

InChI

InChI=1S/C9H11F3O4/c1-3-15-5-6(8(14)16-4-2)7(13)9(10,11)12/h5H,3-4H2,1-2H3

InChIKey

XNGGOXOLHQANRB-WAYWQWQTSA-N

SMILES

C(OCC)(=O)C(=COCC)C(=O)C(F)(F)F

CAS DataBase Reference

571-55-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-23

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29171900

MSDS

• Language:English Provider:SigmaAldrich

Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate Usage And Synthesis

Uses

Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutyrate may be employed as a starting reagent for the synthesis of 1-methyl-3-trifluoromethyl-1H-pyrazole-4- carboxylic acid.

General Description

Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutyrate has been reported to participate in the microwave-assisted synthesis of ethyl 1-[4-(2,3,3-trichloroacrylamido)phenyl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate.

Synthesis

General procedure for the synthesis of ethyl ethoxy-2-methylene trifluoroacetoacetate from triethyl orthoformate and ethyl trifluoroacetoacetate: ethyl 4,4,4-trifluoro-3-oxobutanoate (30 g, 162.9 mmol) was added to a solution of acetic anhydride (50 mL) containing triethoxymethane (72.4 g, 488.8 mmol). The reaction mixture was stirred continuously at 135 °C for 18 hours. Upon completion of the reaction, the brown mixture was concentrated to afford ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate (38 g, 97.1% yield), the product was a brown oil that could be used in subsequent reactions without further purification. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 1.23-1.33 (m, 3H), 1.40 (dt, J = 14.18, 7.19 Hz, 3H), 4.19-4.36 (m, 4H), 7.66-7.87 (m, 1H).

References

[1] Journal of medicinal chemistry, 2000, vol. 43, # 21, p. 3995 - 4004
[2] Patent: US2018/170909, 2018, A1. Location in patent: Paragraph 0824; 0825
[3] Patent: CN106432183, 2017, A. Location in patent: Paragraph 0031; 0032
[4] Patent: WO2016/151403, 2016, A1. Location in patent: Paragraph 00520
[5] Journal of Molecular Structure, 2018, vol. 1171, p. 631 - 638

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