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395315

Sigma-Aldrich

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:
2009-97-4
Molecular Weight:
156.14
MDL number:
MFCD09039264
UNSPSC Code:
12352100
PubChem Substance ID:
24864652
NACRES:
NA.22

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

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_germany

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

Certificates of Analysis (COA)

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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)
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)
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)
M Yang et al.
The Journal of organic chemistry, 66(20), 6729-6733 (2001-10-02)
The Rh(2)(OAc)(4)-stabilized carbenoid derived from dimethyl diazomalonate has been found to insert into the N-H bond of sterically hindered secondary aliphatic amines to afford hindered tertiary aliphatic amines in quite satisfactory yields. For example dimethyl 2-(dicyclohexylamino)propanedioate was formed in 85%
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