2-METHYL-5-TRIFLUOROMETHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

131-133℃

Boiling point:

288.8±40.0 °C(Predicted)

Density 

1.56±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

crystalline powder

pka

2.55±0.25(Predicted)

color 

White

InChI

InChI=1S/C6H5F3N2O2/c1-11-3(5(12)13)2-4(10-11)6(7,8)9/h2H,1H3,(H,12,13)

InChIKey

AQUQLOWJSBFHBD-UHFFFAOYSA-N

SMILES

N1(C)C(C(O)=O)=CC(C(F)(F)F)=N1

Safety Information

Risk Statements 

22-36/37/38

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

29331990

2-METHYL-5-TRIFLUOROMETHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID Usage And Synthesis

Chemical Properties

White solid

Uses

1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic Acid is used in preparation of arylaminopyridine carboxamides as vanin inhibitors for treatment of vanin-mediated diseases.

Synthesis

General procedure for the synthesis of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid from ethyl 1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate: To a 15 mL Schlenk reaction flask containing ethyl 1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate (1.5 mmol) was added a solution of 1 N sodium hydroxide (2.5 mL), the The resulting mixture was stirred vigorously for 24 h at room temperature. Upon completion of the reaction, the reaction mixture was acidified with 6 N HCl at 0 °C. The resulting solid was collected by filtration and the solid was suspended in dichloromethane. The organic and aqueous layers were separated and the aqueous layer was further extracted with dichloromethane. All organic layers were combined and dried with anhydrous Na2SO4 and subsequently concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent ratio: hexane/EtOAc = 5:1 to 2:1) to afford 1-methyl-3-trifluoromethyl-5-pyrazolecarboxylic acid (275 mg, 95% yield) as a white solid.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 46, p. 4344 - 4347
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 24, p. 6255 - 6258

2-METHYL-5-TRIFLUOROMETHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID(128694-63-3)Related Product Information

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