All Photos(1)
Synonym(s):
Ethyl Α-diazoacetoacetate, Ethyl 2-diazo-3-oxobutanoate
Linear Formula:
CH3COC(N2)CO2C2H5
CAS Number:
Molecular Weight:
156.14
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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.)
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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)
Niobium (V) chloride-catalyzed C-H insertion reactions of ?-diazoesters: synthesis of β-keto esters
Yadav JS, et al.
Tetrahedron, 61(4), 875-878 (2005)
Liangliang Shi et al.
Chemical communications (Cambridge, England), 51(97), 17277-17280 (2015-10-16)
A mild and efficient Rh(III)-catalyzed regioselective synthesis of isoquinolones and pyridones has been developed. The protocol uses readily available N-methoxybenzamide or N-methoxymethacrylamide and diazo compounds as starting materials. The process involving tandem C-H activation, cyclization, and condensation steps proceeds under
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