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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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Related Categories

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
MKCS4068
MKCT6861
MKCQ6362

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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
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)
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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