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E22201

Sigma-Aldrich

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
Beilstein:
107654
MDL number:
MFCD00001989
UNSPSC Code:
12352100
PubChem Substance ID:
24894459
NACRES:
NA.22

form

liquid

Quality Level

200

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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Application

New Diazoacetate Formulations
Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.

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Signal Word

Warning

Hazard Classifications

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

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
MKCS4068
MKCT6861
MKCQ6362
MKCR6267
MKCR6269

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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.
Yoichiro Kuninobu et al.
Chemical communications (Cambridge, England), 46(46), 8860-8862 (2010-10-23)
Treatment of tertiary amines with diazoacetate in the presence of a catalytic amount of an iron salt, FeCl(3), in ethanol gave glycine derivatives. In this reaction, a carbon-nitrogen single bond of the amine was cleaved.
Barry M Trost et al.
Journal of the American Chemical Society, 134(4), 2075-2084 (2011-11-18)
A novel synthetic strategy toward the asymmetric synthesis of vicinal diols bearing a tertiary center is presented. The method encompasses the dinuclear Mg-catalyzed asymmetric addition of ethyl diazoacetate into several aldehydes, oxidation of the diazo functionality, and diastereoselective alkyl transfer
Marianne Lenes Rosenberg et al.
Organic letters, 11(3), 547-550 (2008-12-26)
A structurally characterized Rh(I) iminocarbene complex (N,C)Rh(CO)Cl is activated with AgOTf to act as a highly cis-selective catalyst for the cyclopropanation of substituted styrenes and other alkenes with ethyl diazoacetate (11 examples, 10-99% yield, up to >99% cis-selectivity).
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.
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