Merck
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11627

Sigma-Aldrich

Diethyl azodicarboxylate solution

purum, ~40% in toluene (H-NMR)

Synonym(s):
NSC 679015, Diethoxycarbonyldiazene solution, NSC 3474, DEAD, Unifoam AZ-AE 200, Diethyl azodiformate solution, 1,2-Ethoxycarbonyl diazene solution
Linear Formula:
C2H5OCON=NCOOC2H5
CAS Number:
Molecular Weight:
174.15
Beilstein:
908662
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

purum

form

solid

concentration

~40% in toluene (H-NMR)

refractive index

n20/D 1.47

storage temp.

2-8°C

SMILES string

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

InChI

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

InChI key

FAMRKDQNMBBFBR-BQYQJAHWSA-N

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Application

Reactant for preparation of:
  • Immunostimulants α-Galactosylceramides
  • Cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases
  • Bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase
  • Derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities
  • Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes

Reagent for:
  • Annulation of N-protected imines
  • α-thiocyanation of enolizable ketones with ammonium thiocyanate
  • Diels-Alder reactions
Diethyl azodicarboxylate (DEAD) is a reagent used in the Mitsunobu reaction.
DEAD can also be used as a reagent in the:
  • Synthesis of esters, ethers, amines, and thioethers of alcohols.
  • Oxidation of alcohols to carbonyl derivatives using ZnBr2 as a catalyst via dehydrogenation reaction.
  • Conversion of alcohol to an azide key intermediate in the total synthesis of immunostimulant α-galactosylceramides.
  • Synthesis of aza-β-lactams from aryl(alkyl)ketenes.
  • Synthesis of 1H-1,2,4-triazole-1,4(5H)-dicarboxylate derivatives.
  • Diels-Alder type reactions.

Other Notes

Reagent used in the Mitsunobu reaction, reviews

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 2 - Skin Irrit. 2 - STOT RE 2

Target Organs

Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

105.8 °F - closed cup

Flash Point(C)

41 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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