ETHYL 3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE Chemical Properties

Melting point:

145 °C

Boiling point:

301.3±42.0 °C(Predicted)

Density 

1.397±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

8.26±0.50(Predicted)

color 

White to Light yellow

CAS DataBase Reference

155377-19-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29331990

MSDS

• Language:English Provider:ALFA

ETHYL 3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE Usage And Synthesis

Chemical Properties

White to tan powder

Uses

Ethyl 3-(Trifluoromethyl)pyrazole-4-carboxylate (cas# 155377-19-8) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of ethyl 3-trifluoromethylpyrazole-4-carboxylate from ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate was as follows: hydrazine hydrate (10 g, 0.199 mol) was dissolved in ethanol (400 mL) and the solution was cooled to 0 °C. A solution of ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate (47.03 g, 0.19 mol) in ethanol (200 mL) was added dropwise to this cooled solution over 90 min. The reaction mixture was kept at 0 °C. Subsequently, the reaction solution was slowly warmed to room temperature and stirred continuously for 3 hours. Upon completion of the reaction, the mixture was concentrated to dryness. The resulting residue was dispersed in boiling cyclohexane (200 mL) and then cooled to room temperature. The precipitate was collected by filtration and washed with cyclohexane. Finally, the product was dried under vacuum at 75 °C to afford ethyl 3-trifluoromethylpyrazole-4-carboxylate (compound 3f) as a yellow powder (38.67 g, 95% yield). The melting point of the product was 145 °C. 1H NMR (CDCl3) data: δ 1.40 (t, 3H, J = 7.0 Hz), 4.39 (q, 2H, J = 7.0 Hz), 8.26 (s, 1H), 13.2 (s (br), 1H). 13C NMR (CDCl3) data: δ 14.0, 61.2, 113.4, 121.0 ( q, J = 268 Hz), 135.3, 142.0 (q, J = 38 Hz), 160.8. High-resolution mass spectrometry (HRMS) analysis: calculated value of 207.0381 for C7H7F3N2O2-H; measured value of 207.0377.

References

[1] Tetrahedron, 2011, vol. 67, # 44, p. 8451 - 8457
[2] Patent: WO2016/81918, 2016, A1. Location in patent: Paragraph 00279
[3] Patent: WO2016/151403, 2016, A1. Location in patent: Paragraph 00521
[4] Patent: WO2017/205684, 2017, A1. Location in patent: Paragraph 00692; 00693
[5] Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 47 - 56

ETHYL 3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE(155377-19-8)Related Product Information

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