ethyl-3-methyl-1H-pyrazole-4-carboxylate Chemical Properties

Melting point:

49-52°C

Boiling point:

280.6±20.0 °C(Predicted)

Density 

1.171±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

soluble in Chloroform, Methanol

pka

12.26±0.50(Predicted)

form 

solid

color 

Light yellow to yellow

InChI

InChI=1S/C7H10N2O2/c1-3-11-7(10)6-4-8-9-5(6)2/h4H,3H2,1-2H3,(H,8,9)

InChIKey

HHYVTIKYZUMDIL-UHFFFAOYSA-N

SMILES

N1C=C(C(OCC)=O)C(C)=N1

Safety Information

WGK Germany 

3

HS Code 

2933119000

ethyl-3-methyl-1H-pyrazole-4-carboxylate Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

Shows systemic antifungal activity accompanied by high levels of phytotoxicity.

Synthesis

[1255] To a solution of ethyl 3-oxobutyrate (20.0 g, 153.7 mmol) in tetrahydrofuran (THF, 150 mL) was added N,N-dimethylformamide dimethyl acetal (DMF-DMA, 19.2 g, 161.4 mmol). The reaction mixture was stirred at 70 °C for 2 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure to give the crude product. The crude product was dissolved in ethanol (EtOH, 150 mL) and hydrazine hydrate (NH2NH2-H2O, 9.2 g, 184.4 mmol) was added slowly and dropwise. The mixture was stirred at 80 °C for 16 hours. At the end of the reaction, the ethanol was removed by concentration under reduced pressure. The residue was diluted with brine (80 mL) and extracted with ethyl acetate (200 mL × 2). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford the target compound ethyl 3-methylpyrazole-4-carboxylate (257a, 21.0 g, 87.8% yield) as a pale green solid.1H NMR (CDCl3, 400 MHz): δ 7.96 (s, 1H), 4.29 (q, J = 7.2 Hz, 2H) 2.55 (s, 3H), 1.34 (t, J = 7.2 Hz, 3H).MS (ESI) m/z (M + H) + 154.8.

References

[1] Patent: WO2018/64119, 2018, A1. Location in patent: Paragraph 1255
[2] Patent: WO2016/25918, 2016, A1. Location in patent: Paragraph 105

ethyl-3-methyl-1H-pyrazole-4-carboxylate(85290-78-4)Related Product Information

• ETHYL 3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE
• ETHYL 1,3,5-TRIMETHYL-1H-PYRAZOLE-4-CARBOXYLATE
• ETHYL 5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE
• ETHYL 2-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE
• ETHYL 2-(4-NITROPHENYL)-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE
• ETHYL 1-(4-CHLOROPHENYL)-5-PROPYL-1H-PYRAZOLE-4-CARBOXYLATE
• ETHYL 1-PHENYL-5-PROPYL-1H-PYRAZOLE-4-CARBOXYLATE
• ETHYL 1-(4-CHLOROPHENYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE
• ETHYL 2-(4-FLUOROPHENYL)-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE
• ethyl-3-methyl-1H-pyrazole-4-carboxylate
• ETHYL 3,5-DIMETHYL-1H-4-PYRAZOLECARBOXYLATE
• ETHYL-3-PHENYL PYRAZOLE-4-CARBOXYLATE
• ETHYL 1-(2,4-DIFLUOROPHENYL)-5-METHYLPYRAZOLE-4-CARBOXYLATE
• 1,3-DIMETHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• ethyl 3-hydrazino-5-methyl-1H-pyrazole-4-carboxylate
• ETHYL 1-(4-AMINOPHENYL)-3,5-DIMETHYL-1H-PYRAZOLE-4-CARBOXYLATE
• ETHYL 1-(6-CHLOROPYRIDAZIN-3-YL)-5-METHYL-1H-PYRAZOLE-4-CARBOXYLATE
• ETHYL 1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-5-METHYL-1H-PYRAZOLE-4-CARBOXYLATE