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Merck

E22201

Ethyl diazoacetate

contains ≥13 wt. % dichloromethane

Sinónimos:

DAAE

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Acerca de este artículo

Fórmula lineal:
N=N=CHCOOC2H5
Número CAS:
Peso molecular:
114.10
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
107654
Form:
liquid
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InChI

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

SMILES string

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

InChI key

YVPJCJLMRRTDMQ-UHFFFAOYSA-N

form

liquid

contains

≥13 wt. % dichloromethane

Quality Level

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

Application

Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.

signalword

Warning

Hazard Classifications

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

Clase de almacenamiento

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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Lian-Biao Zhao et al.
The Journal of organic chemistry, 72(26), 10276-10278 (2007-11-29)
Copper-catalyzed [4 + 1] cycloaddition reaction of alpha,beta-acetylenic ketones with alpha-diazo esters offers an efficient, direct route to highly substituted furans. The reaction conditions and the scope of the process are examined, and a possible mechanism is proposed.
Ying Chen et al.
The Journal of organic chemistry, 69(7), 2431-2435 (2004-03-31)
Vitamin B(12) derivatives were found for the first time to be general and efficient catalysts for asymmetric cyclopropanation of alkenes with ethyl diazoacetate (EDA). Among several common derivatives, aquocobalamin (B(12a)) was shown to be the most effective catalyst for a
Marianne Lenes Rosenberg et al.
The Journal of organic chemistry, 76(8), 2465-2470 (2011-03-19)
The performance of recently reported highly cis-diastereoselective Rh(I) cyclopropanation catalysts has been significantly improved by a systematic study of different reaction parameters (catalyst activation, solvent, temperature, stoichiometry). The catalyst efficiency and diastereoselectivity were enhanced by changing the activating agent from
Barry M Trost et al.
Journal of the American Chemical Society, 131(5), 1674-1675 (2009-02-05)
Magnesium-catalyzed enantioselective aldol between ethyl diazoacetate and aromatic, aliphatic, and alpha,beta-unsaturated aldehydes affords alpha-diazo-beta-hydroxy-esters in high enantioselectivities. Aldol adducts resulting from this asymmetric transformation are versatile intermediates toward the synthesis of several ester containing chiral building blocks.
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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