| Identification | Back Directory | [Name]
ETHYL DIAZOACETOACETATE | [CAS]
2009-97-4 | [Synonyms]
ETHYL DIAZOACETOACETATE
Ethyl 2-diazoacetoacetate
2-Diazo-3-oxobutyric acid ethyl
2-Diazoacetoacetic acid ethyl ester
2-Diazo-3-oxobutyric acid ethyl ester
3-Oxo-2-diazobutanoic acid ethyl ester
2-Diazo-3-oxobutanoic acid ethyl ester
Butanoic acid, 2-diazo-3-oxo-, ethyl ester | [Molecular Formula]
C6H8N2O3 | [MDL Number]
MFCD00192140 | [MOL File]
2009-97-4.mol | [Molecular Weight]
156.14 |
| Chemical Properties | Back Directory | [Boiling point ]
102-103 °C(Press: 12 Torr) | [density ]
1.131 g/mL at 25 °C(lit.)
| [vapor pressure ]
0.36 psi ( 20 °C)
| [refractive index ]
n20/D 1.474(lit.)
| [Fp ]
185 °F
| [storage temp. ]
Storage temp. 2-8°C | [form ]
liquid | [Appearance]
Colorless to light yellow Liquid | [InChI]
1S/C6H8N2O3/c1-3-11-6(10)5(8-7)4(2)9/h3H2,1-2H3 | [InChIKey]
JWTPSIXYXYNAOU-UHFFFAOYSA-N | [SMILES]
CCOC(=O)C(=[N+]=[N-])C(C)=O |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3
| [HS Code ]
29270000 | [Storage Class]
5.2 - Organic peroxides and self-reacting hazardous materials | [Hazard Classifications]
Eye Irrit. 2
Self-react. C
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
Ethyl diazoacetoacetate can be used as a reactant to synthesize:
- 1,4-oxathiocines and thiopyran derivatives via Rh-catalyzed reaction with 2-amino-4,5-dihydro-3-thiophenecarbonitriles.
- β-keto esters via C-H insertion reaction with aromatic aldehydes using NbCl5 as a catalyst.
- Diazoacetoacetate derivatives by reacting with aldehydes via aldol condensation and subsequent and in situ oxidation reaction.
- Isoquinolone and pyridone derivatives by Rh-catalyzed C-H activation/annulation reaction with various N-methoxybenzamides.
| [Synthesis Reference(s)]
Tetrahedron Letters, 5, p. 2285, 1964 DOI: 10.1002/lipi.19640660210 | [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. |
|
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Energy Chemical
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