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E22201

Sigma-Aldrich

Ethyl diazoacetate

contains ≥13 wt. % dichloromethane

Synonym(s):

DAAE

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About This Item

Linear Formula:
N=N=CHCOOC2H5
CAS Number:
623-73-4
Molecular Weight:
114.10
Beilstein:
107654
MDL number:
MFCD00001989
UNSPSC Code:
12352100
PubChem Substance ID:
24894459
NACRES:
NA.22

form

liquid

Quality Level

200

contains

≥13 wt. % dichloromethane

refractive index

n20/D 1.46 (lit.)

bp

140-141 °C/720 mmHg (lit.)

mp

−22 °C (lit.)

density

1.085 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)C=[N+]=[N-]

InChI

1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3

InChI key

YVPJCJLMRRTDMQ-UHFFFAOYSA-N

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Application

New Diazoacetate Formulations
Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.

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Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 3 - Self-react. E - Skin Irrit. 2

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

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Pierre de Frémont et al.
Chemical communications (Cambridge, England), (19)(19), 2045-2047 (2006-06-13)
A number of cationic gold(I) complexes have been synthesized and found to be stabilized by the use of N-heterocyclic carbene ligands. These species are often employed as in situ-generated reactive intermediates in gold catalyzed organic transformations. An isolated, well-defined species
Eva M Reingruber et al.
Journal of chromatography. A, 1255, 259-266 (2012-03-31)
Polymers, especially copolymers, are highly complex samples and, therefore, require various setups for their thorough characterization. In this work, one- and two-dimensional chromatographic approaches were applied to characterize two homopolymers and two dissimilar copolymers prepared by rhodium-mediated carbene polymerization using
Palladium-catalyzed cross-coupling of aryl or vinyl iodides with ethyl diazoacetate.
Cheng Peng et al.
Journal of the American Chemical Society, 129(28), 8708-8709 (2007-06-26)
Detian Gao et al.
The Journal of organic chemistry, 73(20), 8057-8068 (2008-09-19)
Several representative acetylenic sulfones were immobilized on a polymer support derived from Merrifield resin by means of ester linkers that were used to couple free carboxylic acid groups on the solid support with benzylic hydroxyl functions on the arylsulfonyl moieties
Chan Pil Park et al.
The Journal of organic chemistry, 74(16), 6231-6236 (2009-07-28)
Formal aromatic C-H insertion of rhodium(II) carbenoid was intensively investigated to develop a new methodology and probe its mechanism. Contrasting with the previously proposed direct C-H insertion, the mechanism was revealed to be electrophilic aromatic substitution, which was supported by
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