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395315 Sigma-Aldrich

Ethyl diazoacetoacetate

  • CAS Number 2009-97-4

  • Linear Formula CH3COC(N2)CO2C2H5

  • Molecular Weight 156.14

  •  MDL number MFCD09039264

  •  PubChem Substance ID 24864652

  •  NACRES NA.22

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Properties

Related Categories Azo/Diazo Compounds, Building Blocks, Chemical Synthesis, Nitrogen Compounds - Organic Building Blocks, Organic Building Blocks More...
vapor pressure   0.36 psi ( 20 °C)
availability   available only in USA
refractive index   n20/D 1.474 (lit.)
density   1.131 g/mL at 25 °C (lit.)
storage temp.   room temp
SMILES string   CCOC(=O)C(=[N+]=[N-])C(C)=O
InChI   1S/C6H8N2O3/c1-3-11-6(10)5(8-7)4(2)9/h3H2,1-2H3
InChI key   JWTPSIXYXYNAOU-UHFFFAOYSA-N

Description

General description

Ethyl diazoacetoacetate is a diazo compound. It participates in Rh2(OAc)4-catalyzed reactions with arylalkylamines and diarylamines. Reaction of ethyl diazoacetoacetate with N-methyl pyrrole and pyrrole derivatives has been studied.

Application

Ethyl diazoacetoacetate may be used in the preparation of diazoacetoacetate derivatives, via one-pot process involving initial DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene)-promoted Aldol condensation. It may be used in the preparation of β-keto esters, via reaction with aldehydes in the presence of NbCl5 in dichloromethane.

Packaging

1 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
Personal Protective Equipment 
WGK Germany 
WGK 3
Flash Point(F) 
185.0 °F - closed cup
Flash Point(C) 
85 °C - closed cup

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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