395315
Ethyl diazoacetoacetate
Synonym(s):
Ethyl Α-diazoacetoacetate, Ethyl 2-diazo-3-oxobutanoate
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About This Item
Linear Formula:
CH3COC(N2)CO2C2H5
CAS Number:
Molecular Weight:
156.14
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Form:
liquid
vapor pressure
0.36 psi ( 20 °C)
form
liquid
availability
available only in USA
refractive index
n20/D 1.474 (lit.)
density
1.131 g/mL at 25 °C (lit.)
functional group
ester, ketone
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
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 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.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
5.2 - Organic peroxides and self-reacting hazardous materials
wgk
WGK 3
flash_point_f
185.0 °F - closed cup
flash_point_c
85 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Related Content
Reaction of dimethyl diazomalonate and ethyl 2-diazoacetoacetate with N-methylpyrrole.
Maryanoff BE.
The Journal of Organic Chemistry, 47(15), 3000-3002 (1982)
Niobium (V) chloride-catalyzed C-H insertion reactions of a-diazoesters: synthesis of ?-keto esters.
Yadav JS, et al.
Tetrahedron, 61(4), 875-878 (2005)
Synthesis of 1, 4-Oxathiocines and Thiopyrans by the Reaction of 2-Amino-4, 5-dihydro-3-thiophenecarbonitriles with Ethyl Diazoacetoacetate
Yamagata K, et al.
Liebigs Annalen der Chemie , 1996(5), 725-729 (1996)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 395315-1G | 04061837633782 |