E22201
Ethyl diazoacetate
contains ≥13 wt. % dichloromethane
Synonym(s):
DAAE
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About This Item
Linear Formula:
N=N=CHCOOC2H5
CAS Number:
Molecular Weight:
114.10
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
107654
Form:
liquid
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
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
Related Categories
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
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
Regulatory Information
危险化学品
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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
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.
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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