ETHYL 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE Chemical Properties

Melting point:

60-61°C

Boiling point:

267.4±40.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-2.85±0.10(Predicted)

form 

solid

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C8H9F3N2O2/c1-3-15-7(14)5-4-13(2)12-6(5)8(9,10)11/h4H,3H2,1-2H3

InChIKey

ZZEXDJGNURSJOF-UHFFFAOYSA-N

SMILES

N1(C)C=C(C(OCC)=O)C(C(F)(F)F)=N1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29309090

ETHYL 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE Usage And Synthesis

Chemical Properties

White solid

Synthesis

Ethyl 3-trifluoromethyl-1H-pyrazole-4-carboxylate (2.0 g, 9.61 mmol) was dissolved in N,N-dimethylformamide (20 mL) and the solution was cooled to 0 °C. Sodium hydride (0.58 g, 14.42 mmol, 60% dispersed in mineral oil) was slowly added to the solution at 0 °C and the reaction mixture was stirred for 20 min. Subsequently, iodomethane (0.90 mL, 14.42 mmol) was added and the reaction mixture was gradually warmed to room temperature over 18 hours. Upon completion of the reaction, the mixture was partitioned between ethyl acetate (100 mL) and water (50 mL). The organic layer was separated and washed sequentially with water (5 x 50 mL) and saturated aqueous sodium chloride solution (50 mL). The organic layer was dried with anhydrous sodium sulfate, filtered, concentrated and purified by silica gel column chromatography (eluent: 90:10 hexane/ethyl acetate) to afford ethyl 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylate (1.74 g, 81.7% yield).1H-NMR (400 MHz, CDCl3) δ 7.92 (s, 1H), 4.27 (q, 2H ), 3.95 (s, 3H), 1.33 (t, 3H).

References

[1] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4569 - 4574
[2] Angew. Chem., 2017, vol. 129, # 16, p. 4640 - 4645,6
[3] Patent: WO2008/141020, 2008, A1. Location in patent: Page/Page column 50
[4] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218

ETHYL 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE(111493-74-4)Related Product Information

• 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID
• 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE
• ETHYL 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE
• 3-(Trifluoromethyl)pyrazole
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