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E22201

Sigma-Aldrich

Ethyl diazoacetate

contains ≥13 wt. % dichloromethane

Synonym(s):

DAAE

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1 KG
₹1,33,829.48

About This Item

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

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form

liquid

Quality Level

contains

≥13 wt. % dichloromethane

refractive index

n20/D 1.46 (lit.)

bp

140-141 °C/720 mmHg (lit.)

mp

−22 °C (lit.)

solubility

water: slightly soluble

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

Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.[1]

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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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Jian-Wu Xie et al.
Organic & biomolecular chemistry, 7(21), 4352-4354 (2009-10-16)
The one-pot synthesis of multisubstituted pyrazole derivatives was achieved via catalyst-free 1,3-dipolar cycloaddition of ethyl diazoacetate and nitroalkenes as the key step and elimination of the leaving group (NO(2) or Br) followed by intramolecular proton transfer with satisfactory yields.
Iris Aviv et al.
Chemical communications (Cambridge, England), (43)(43), 4477-4479 (2007-02-08)
Iron complexes of porphyrins (and corroles to a lesser extent) are the first catalysts to utilize ammonia for the synthesis of N-free amino acid esters.
Lidia Dumitrescu et al.
Organic letters, 13(4), 692-695 (2011-01-21)
The insertion reaction of diazocarbonyls to acids could be performed smoothly in fluorinated alcohols in the absence of metal catalyst. This new procedure allowed the chemoselective preparation of various functionalized compounds such as acyloxyesters, depsipeptides, and sulfonate, phosphonate, or boronate
Sun-Liang Cui et al.
Journal of the American Chemical Society, 130(41), 13526-13527 (2008-09-19)
A general and concise synthesis of functionalized indoles via domino reaction of N-aryl amides and ethyl diazoacetate has been developed. The methodology offers a great potential for the synthesis of biologically active and naturally occurring indole derivatives.
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

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