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
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
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
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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.
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.
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