1-METHYL-3-PROPYLPYRAZOLE-5-CARBOXYLIC ACID Chemical Properties

Melting point:

150-154 °C

Boiling point:

330.3±30.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Sightly), Methanol (Slightly)

form 

Solid

pka

3.10±0.25(Predicted)

color 

Off-White to Pale Beige

CAS DataBase Reference

139755-99-0(CAS DataBase Reference)

Safety Information

Risk Statements 

20/21/22

Safety Statements 

3/9-24/25-36/37

HazardClass 

IRRITANT

HS Code 

29331990

1-METHYL-3-PROPYLPYRAZOLE-5-CARBOXYLIC ACID Usage And Synthesis

Chemical Properties

White solid

Uses

Intermediate in the production of Sildenafil and respective analogs.

Synthesis

Preparation of Intermediate I-04a: Ethyl 1-methyl-3-n-propyl-pyrazole-5-carboxylate (11 g, 56.12 mmol) was dissolved in 6 M hydrochloric acid solution (121 mL) and heated to 100°C for overnight reaction. Upon completion of the reaction, the mixture was concentrated under vacuum and subsequently extracted with ethyl acetate (EA) and the organic layer was washed with water. Finally, the organic layer was concentrated in vacuum to afford the target product 1-methyl-3-propyl-1H-pyrazole-5-carboxylic acid (I-04a) (9.4 g, 98% yield).ESI-MS (M + 1): 169; calculated value C8H12N2O2: 168.1.

References

[1] Patent: WO2014/131855, 2014, A1. Location in patent: Page/Page column 80
[2] Patent: WO2016/20307, 2016, A1. Location in patent: Page/Page column 50
[3] Patent: US2008/194529, 2008, A1. Location in patent: Page/Page column 56-57
[4] Patent: WO2015/114647, 2015, A1. Location in patent: Page/Page column 46; 47
[5] Patent: US5250534, 1993, A

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