| Identification | More | [Name]
Ethyl pyrazole-4-carboxylate | [CAS]
37622-90-5 | [Synonyms]
ETHYL 4-PYRAZOLECARBOXYLATE
ETHYL PYRAZOLE-4-CARBOXYLATE
PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
Ethyl 1H-pyrazole-4-carboxylate
Ethyl 4-pyarazolecarboxylate
Ethyl pyrazole-4-carboxylate 98+%
1H-Pyrazole-4-carboxylicacid,ethylester(9CI)
Ethyl 4-pyrazolecarboxylate, 99%-See B25351
1H-Pyrazole-4-carboxylic acid ethyl ester | [EINECS(EC#)]
609-452-9 | [Molecular Formula]
C6H8N2O2 | [MDL Number]
MFCD00010844 | [Molecular Weight]
140.14 | [MOL File]
37622-90-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White to pale yellow crystalline powder | [Melting point ]
78-80 °C (lit.) | [Boiling point ]
138-140 °C/3 mmHg (lit.) | [density ]
1.2850 (rough estimate) | [refractive index ]
1.5010 (estimate) | [Fp ]
138-140°C/3mm | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Miscible with acetone. | [form ]
Crystalline Powder | [pka]
11.70±0.50(Predicted) | [color ]
White to pale yellow | [InChI]
InChI=1S/C6H8N2O2/c1-2-10-6(9)5-3-7-8-4-5/h3-4H,2H2,1H3,(H,7,8) | [InChIKey]
KACZQOKEFKFNDB-UHFFFAOYSA-N | [SMILES]
N1C=C(C(OCC)=O)C=N1 | [LogP]
0.909 (est) | [CAS DataBase Reference]
37622-90-5(CAS DataBase Reference) | [NIST Chemistry Reference]
4-(C2H5COO)-pyrazole(37622-90-5) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29331990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to pale yellow crystalline powder | [Uses]
Ethyl pyrazole-4-carboxylate is used for the synthesis of isoxazole-4-carboxylic acid derivatives and isoxazole-3,5-dicarboxamides.
| [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 30, p. 865, 1993 DOI: 10.1002/jhet.5570300404 | [Synthesis]
The general procedure for the synthesis of ethyl 4-pyrazolecarboxylate from ethyl 2-formyl-3-oxopropanoate was as follows: 6.2 g (193 mmol) of hydrazine was slowly added to a solution of 27.6 g (192 mmol) of (ethoxycarbonyl)malondialdehyde dissolved in 150 mL of ethanol under ice bath cooling conditions. The reaction mixture was stirred at room temperature for 17 hours to complete the reaction. Subsequently, ethanol was removed from the reaction mixture by vacuum distillation. The residue was purified by silica gel column chromatography using a solvent mixture of dichloromethane and ethyl acetate as the unfolding agent, resulting in 19.4 g (72.4% yield) of ethyl 1H-pyrazole-4-carboxylate as yellow crystals.1H-NMR [CDCl3/TMS, δ (ppm)]: 8.08 (2H, s), 5.30 (1H, s), 4.31 ( 2H, q), 1.36 (3H, t). | [References]
[1] Tetrahedron, 2008, vol. 64, # 33, p. 7745 - 7758
[2] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 865 - 872
[3] Patent: EP1364946, 2003, A1. Location in patent: Page/Page column 196
[4] Patent: US2005/256004, 2005, A1. Location in patent: Page/Page column 32 |
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