E22201

Sigma-Aldrich

Ethyl diazoacetate

contains ≥13 wt. % dichloromethane

Synonym(s):
DAAE
Linear Formula:
N=N=CHCOOC2H5
CAS Number:
Molecular Weight:
114.10
Beilstein/REAXYS Number:
107654
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

contains

≥13 wt. % dichloromethane

refractive index

n20/D 1.46 (lit.)

bp

140-141 °C/720 mmHg (lit.)

mp

−22 °C (lit.)

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

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Related Categories

Application

Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.

Packaging

5 g in glass bottle
20, 100 g in poly bottle
1 kg in poly bottle

Signal Word

Warning

hazcat

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 3 - Self-react. E - Skin Irrit. 2

storage_class_code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK Germany

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Certificate of Analysis

Certificate of Origin

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...
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...
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...
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)
Tetrahedron Letters, 45, 5649-5649 (2004)

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