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Merck

E22201

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24894459
MDL number:
MFCD00001989
Beilstein/REAXYS Number:
107654

Key Documents

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Product Name

Ethyl diazoacetate, contains ≥13 wt. % dichloromethane

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

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

Quality Level

200

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Application

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

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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

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCX3455
MKCW9559
MKCT6861
MKCS4068
MKCQ6362

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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.
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
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
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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