| Identification | Back Directory | [Name]
Ethyl malonyl hydrazide | [CAS]
30866-24-1 | [Synonyms]
Nsc75205
ETHYL MALONYL HYDRAZIDE
Ethyl malonyl hydrazine
N1-Ethylmalonohydrazide
ETHYL 3-HYDRAZINO-3-OXOPROPIONATE
Ethyl 3-oxo-3-hydrazino-propionate
ethyl 3-hydrazinyl-3-oxopropanoate
ethyl 2-(hydrazinecarbonyl)acetate
Ethyl 3-hydrazino-3-oxopropionate 97%
Propanedioic acid, 1-ethyl ester, 3-hydrazide | [Molecular Formula]
C5H10N2O3 | [MDL Number]
MFCD00134484 | [MOL File]
30866-24-1.mol | [Molecular Weight]
146.14 |
| Chemical Properties | Back Directory | [Melting point ]
72-75 °C (lit.) | [Boiling point ]
320.9±25.0 °C(Predicted) | [density ]
1.176±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [form ]
solid | [pka]
12.02±0.35(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C5H10N2O3/c1-2-10-5(9)3-4(8)7-6/h2-3,6H2,1H3,(H,7,8) | [InChIKey]
HCPOCMMGKBZWSJ-UHFFFAOYSA-N | [SMILES]
C(C(=O)NN)C(=O)OCC |
| Hazard Information | Back Directory | [Uses]
Ethyl 3-hydrazino-3-oxopropionate may be used in the following studies:
- As starting reagent in the step-wise construction of complex pyrrole-pyrazole system.,
- Synthesis of 4,5-dihydro-1H-pyrazoles, via reaction with 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones, using conventional thermal heating method and a microwave-assisted method.
- Synthesis of pyrazolopyridazine.
| [Synthesis]
General procedure for the synthesis of ethyl 3-oxo-3-hydrazinopropionate from diethyl malonate: diethyl malonate (10 g, 62.5 mmol) was dissolved in 50 ml of anhydrous ethanol, followed by slow addition of 85% hydrazine hydrate (1.44 g, 1.44 mol). The reaction mixture was stirred and reacted at room temperature overnight. After completion of the reaction, filtration was carried out and the filtrate was collected. The solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by recrystallization with a mixed solvent of ethyl acetate/petroleum ether to finally obtain the target compound ethyl 3-oxo-3-hydrazinopropionate (2.10 g, 64% yield) as a white solid. | [References]
[1] Patent: CN107629014, 2018, A. Location in patent: Paragraph 0016; 0017
[2] European Journal of Medicinal Chemistry, 2008, vol. 43, # 3, p. 584 - 594
[3] Liebigs Annalen der Chemie, 1990, # 9, p. 841 - 846
[4] European Journal of Medicinal Chemistry, 2013, vol. 70, p. 358 - 363
[5] Chinese Chemical Letters, 2017, vol. 28, # 5, p. 1031 - 1034 |
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