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378909

Sigma-Aldrich

Ethyl 3-hydrazino-3-oxopropionate

97%

Synonym(s):

Ethyl malonyl hydrazide

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About This Item

Linear Formula:
H2NNHCOCH2CO2C2H5
CAS Number:
Molecular Weight:
146.14
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

solid

mp

72-75 °C (lit.)

functional group

amine
ester
hydrazine

SMILES string

CCOC(=O)CC(=O)NN

InChI

1S/C5H10N2O3/c1-2-10-5(9)3-4(8)7-6/h2-3,6H2,1H3,(H,7,8)

InChI key

HCPOCMMGKBZWSJ-UHFFFAOYSA-N

Application

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Sequential Construction of Complex Pyrrole-Pyrrole or Pyrrole-Pyrazole Systems from 1, 2-Diaza-1, 3-butadienes.
Attanasi OA, et al.
Synlett, 09, 1367-1370 (1999)
Miguel F Braña et al.
Journal of medicinal chemistry, 48(22), 6843-6854 (2005-10-28)
Pyrazolopyridazine 1a was identified in a high-throughput screening carried out by BASF Bioresearch Corp. (Worcester, MA) as a potent inhibitor of CDK1/cyclin B and shown to have selectivity for the CDK family. Analogues of the lead compound have been synthesized
Regioselective role of the hydrazide moiety in the formation of complex pyrrole-pyrazole systems
Attanasi OA, et al.
Tetrahedron, 57(7), 1387-1394 (2001)
An E-factor minimized solvent-free protocol for the preparation of 4, 5-dihydro-5-(trifluoromethyl)-1H-pyrazoles.
Buriol L, et al.
Monatshefte fur Chemie / Chemical Monthly, 142(5), 515-520 (2011)

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