1-Methyl-1H-pyrazol-4-ol Chemical Properties

Boiling point:

217.7±13.0 °C(Predicted)

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.19±0.14(Predicted)

form 

solid

color 

Cream

Safety Information

HS Code 

2933119000

1-Methyl-1H-pyrazol-4-ol Usage And Synthesis

Uses

1-Methyl-1H-pyrazol-4-ol is used as a storage and transport stabiliser for polymerised compounds and as an intermediate in the preparation of pyrazole herbicides (1-methyl-5hydroxypyrazole).

Synthesis

General procedure for the synthesis of 1-methyl-4-hydroxy-1H-pyrazole from 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole: To 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 120.2 mmol) was added slowly, under the condition of 0 °C (ice bath cooling), to a 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole ( 25.0 g, 120.2 mmol) in tetrahydrofuran solution (600.9 mL, 0.2 M) was slowly added to aqueous sodium hydroxide solution (80.1 mL, 3 M, 240.3 mmol) followed by hydrogen peroxide (27.3 mL, 240.3 mmol). The reaction mixture was stirred at 0-25°C for 3 hours. After completion of the reaction, the reaction mixture was neutralized in a small heart with 12N hydrochloric acid (18.6 mL) and diluted with a solvent mixture of dichloromethane and methanol (90:10, 200 mL). The aqueous layer was extracted with a solvent mixture of dichloromethane and methanol (90:10, 3 x 200 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford the target product 1-methyl-4-hydroxy-1H-pyrazole.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 49, p. 4587 - 4590
[2] Patent: WO2016/11930, 2016, A1. Location in patent: Page/Page column 138
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1370 - 1387