| Identification | Back Directory | [Name]
Dimethyl 1H-pyrazole-3,5-dicarboxylate | [CAS]
4077-76-3 | [Synonyms]
3,5-Dicarbomethoxypyrazole
3,5-Bis(methoxycarbonyl)pyrazole
Dimethyl 3,5-pyrazoledicarboxylate
3,5-Bis(methoxycarbonyl)-1H-pyrazole
Dimethyl 1H-pyrazol-3,5-dicarboxylate
3,5-dimethyl 1H-pyrazole-3,5-dicarboxylate
Pyrazole-3,5-dicarboxylic acid dimethyl ester
1H-Pyrazole-3,5-dicarboxylic acid dimethyl ester
1H-Pyrazole-3,5-dicarboxylic acid 3,5-dimethyl ester | [Molecular Formula]
C7H8N2O4 | [MDL Number]
MFCD00975602 | [MOL File]
4077-76-3.mol | [Molecular Weight]
184.15 |
| Chemical Properties | Back Directory | [Melting point ]
151-152℃ | [Boiling point ]
344℃ | [density ]
1.346 | [Fp ]
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 |
| Hazard Information | Back Directory | [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 |
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