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Merck
CN

D90008

Diethyl azodicarboxylate

Synonym(s):

DEAD

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About This Item

Linear Formula:
C2H5OCON=NCOOC2H5
CAS Number:
1972-28-7
Molecular Weight:
174.15
EC Number:
217-821-7
UNSPSC Code:
12352108
PubChem Substance ID:
329798884
Beilstein/REAXYS Number:
908662
MDL number:
MFCD00009103

Key Documents

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InChI key

FAMRKDQNMBBFBR-BQYQJAHWSA-N

InChI

1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+

SMILES string

CCOC(=O)\N=N\C(=O)OCC

form

liquid

impurities

<3% dichloromethane

refractive index

n20/D 1.43 (lit.)

bp

106 °C/13 mmHg (lit.)

density

1.106 g/mL at 25 °C (lit.)

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Application

Reagent used in Mitsunobu and Diels-Alder reactions, as well as in allylic amination of alkenes.

pictograms

Exploding BombExclamation mark
GHS01,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Expl. 1.1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

1 - Explosive hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
04823BW
15914EF
10614JS
10114KZ
09615PY

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The Journal of Organic Chemistry, 58, 4979-4979 (1993)
F K Brown et al.
Journal of medicinal chemistry, 37(5), 674-688 (1994-03-04)
Systematic modification of the presumed P1 side chain in a series of (carboxyalkyl)amino-based inhibitors of matrix metalloproteinases enabled identification of the 2-(1,3-dihydro-1,3-dioxo-2H-benz[f]isoindol-2-yl)ethyl group as a preferred substituent imparting potent inhibition of the enzymes collagenase and gelatinase. It was subsequently found
The Journal of Organic Chemistry, 58, 5261-5261 (1993)
Gregory S Watson et al.
Acta biomaterialia, 21, 109-122 (2015-03-17)
Geckos, and specifically their feet, have attracted significant attention in recent times with the focus centred around their remarkable adhesional properties. Little attention however has been dedicated to the other remaining regions of the lizard body. In this paper we
Basile Siewe et al.
PloS one, 9(4), e92934-e92934 (2014-04-18)
During HIV infection, IL-10/IL-10 receptor and programmed death-1 (PD-1)/programmed death-1-ligand (PD-L1) interactions have been implicated in the impairment of cytotoxic T lymphocyte (CTL) activity. Despite antiretroviral therapy (ART), attenuated anti-HIV CTL functions present a major hurdle towards curative measures requiring
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