Dimethyl 1H-pyrazole-3,5-dicarboxylate Chemical Properties

Melting point:

151-152℃

Boiling point:

344℃

Density 

1.346

Flash point:

162℃

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

8.08±0.10(Predicted)

color 

White

InChI

InChI=1S/C7H8N2O4/c1-12-6(10)4-3-5(9-8-4)7(11)13-2/h3H,1-2H3,(H,8,9)

InChIKey

SIPQVJNEQSWAOK-UHFFFAOYSA-N

SMILES

N1C(C(OC)=O)=CC(C(OC)=O)=N1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933199090

Dimethyl 1H-pyrazole-3,5-dicarboxylate Usage And Synthesis

Uses

Dimethyl 1H-Pyrazole-3,5-dicarboxylate is used in preparation of substituted Dihydropyrazolopyrazinecarboxamide derivatives as EP3 receptor antagonists useful for treating diseases.

Synthesis

The general procedure for the synthesis of dimethyl 1H-pyrazole-3,5-dicarboxylate from methanol and 3,5-pyrazoledicarboxylic acid was as follows: 31.7 g (0.203 mol) of 3,5-pyrazoledicarboxylic acid was mixed with 125 mL of methanol and the mixture was saturated with gaseous HCl. The reaction mixture was heated to reflux for 3 hours and subsequently left to stand overnight at room temperature. After completion of the reaction, the precipitate was collected by filtration and washed with methanol. A final 23.5 g (63% yield) of white crystalline product with a melting point of 142-143 °C was obtained. The structure of the product was confirmed by IR spectroscopy, and the main absorption peaks were 3105 cm-1 (broad peak, NH stretching vibration), 1710 cm-1 (strong peak, C=O stretching vibration), and 1240 cm-1 (strong peak, C-O-C stretching vibration).1H NMR spectroscopic data were as follows: δ 3.82 (single peak, 6H, CH3), δ 6.36 (single peak, 1H, pyrazolyl ring 4-H), δ 14.5 (single peak, 1H, pyrazolyl ring 4-H), and δ 14.5 (single peak, 1H). 4-H), δ 14.43 (single peak, 1H, NH).

References

[1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
[2] Journal of Organic Chemistry, 1999, vol. 64, # 21, p. 7751 - 7755
[3] Asian Journal of Chemistry, 2015, vol. 27, # 7, p. 2545 - 2547
[4] Russian Journal of Organic Chemistry, 2016, vol. 52, # 9, p. 1322 - 1325
[5] Zh. Org. Khim., 2016, vol. 52, # 9, p. 1334 - 1337,4

Dimethyl 1H-pyrazole-3,5-dicarboxylate(4077-76-3)Related Product Information

• 1H-PYRAZOLE-3-CARBONITRILE
• DIETHYL 3,5-PYRAZOLEDICARBOXYLATE
• Pyrazole-3-boronic acid
• Methyl Pyrazole-3-carboxylate
• 4-CYANOPYRAZOLE
• 5-Pyrazolecarboxylic acid
• 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE)-PYRAZOLE
• Pyrazole