Ethyl malonyl hydrazide Chemical Properties

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2928009090

MSDS

• Language:English Provider:SigmaAldrich

Ethyl malonyl hydrazide Usage And Synthesis

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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