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
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Palladium-catalyzed cross-coupling of aryl or vinyl iodides with ethyl diazoacetate.
Cheng Peng et al.
Journal of the American Chemical Society, 129(28), 8708-8709 (2007-06-26)
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
Chan Pil Park et al.
The Journal of organic chemistry, 74(16), 6231-6236 (2009-07-28)
Formal aromatic C-H insertion of rhodium(II) carbenoid was intensively investigated to develop a new methodology and probe its mechanism. Contrasting with the previously proposed direct C-H insertion, the mechanism was revealed to be electrophilic aromatic substitution, which was supported by
Detian Gao et al.
The Journal of organic chemistry, 73(20), 8057-8068 (2008-09-19)
Several representative acetylenic sulfones were immobilized on a polymer support derived from Merrifield resin by means of ester linkers that were used to couple free carboxylic acid groups on the solid support with benzylic hydroxyl functions on the arylsulfonyl moieties
Tat-Shing Lai et al.
Dalton transactions (Cambridge, England : 2003), (40)(40), 4845-4851 (2006-10-13)
With the iron(III) complex of the Halterman iron porphyrin [P*Fe(Cl)] and ethyl diazoacetate (EDA) as catalyst and carbene source, respectively, styrene-type substrates were converted to cyclopropyl esters with high trans/cis ratio (not less than 12) and high enantioselectivity for the
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