1-Methyl-1H-pyrazole-3-carboxylic acid Chemical Properties

Melting point:

150-152 ºC

Boiling point:

306.9±15.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.05±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C5H6N2O2/c1-7-3-2-4(6-7)5(8)9/h2-3H,1H3,(H,8,9)

InChIKey

YBFIKNNFQIBIQZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

25016-20-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933199090

MSDS

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1-Methyl-1H-pyrazole-3-carboxylic acid Usage And Synthesis

Uses

1-Methyl-1H-pyrazole-3-carboxylic acid is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Definition

ChEBI: 1-methyl-pyrazole-3-carboxylic acid is a member of the class of pyrazoles that is N-methylpyrazole substituted by a carboxy group at position 3. It has a role as a metabolite. It is a member of pyrazoles and a monocarboxylic acid. It is functionally related to a N-methylpyrazole.

Synthesis

Over 45 minutes, dimethyl sulfate (236 g, 177 mL, 1.87 mol) was slowly added dropwise to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) dissolved in 20% aqueous sodium hydroxide (850 mL) at 40 °C. The reaction mixture was heated at 80 °C for 2 h and subsequently cooled to room temperature. The reaction mixture was filtered and the filtrate was acidified to pH 1 with concentrated hydrochloric acid, the precipitate was collected by filtration, washed with water and dried under vacuum to afford 1-methyl-1H-pyrazole-5-carboxylic acid (85 g, 38% yield). The remaining filtrate was concentrated to 800 mL in vacuum and extracted with chloroform (15 x 400 mL) several times. The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated in vacuum to remove the solvent. The residue was recrystallized by isopropanol to give 1-methyl-1H-pyrazole-3-carboxylic acid (74 g) as a white crystalline solid.

References

[1] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, # 11, p. 2291 - 2296
[2] Zhurnal Obshchei Khimii, 1982, vol. 52, # 11, p. 2592 - 2598
[3] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, # 11, p. 2291 - 2296
[4] Zhurnal Obshchei Khimii, 1982, vol. 52, # 11, p. 2592 - 2598
[5] Patent: WO2004/58702, 2004, A2. Location in patent: Page 30-31; 24

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