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11627

Sigma-Aldrich

Diethyl azodicarboxylate solution

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

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Synonym(s):
1,2-Ethoxycarbonyl diazene solution, DEAD, Diethoxycarbonyldiazene solution, Diethyl azodiformate solution, NSC 3474, NSC 679015, Unifoam AZ-AE 200
Linear Formula:
C2H5OCON=NCOOC2H5
CAS Number:
1972-28-7
Molecular Weight:
174.15
Beilstein:
908662
MDL number:
MFCD00009103
UNSPSC Code:
12352108
PubChem Substance ID:
57646942
NACRES:
NA.22

grade

purum

Quality Level

100

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

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.

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

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 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Phosphine-mediated annulation of N-protected imines with DEAD
Lian Z, et al.
Tetrahedron, 67(11), 2018-2024 (2011)
Synthesis and thermolysis of Diels-Alder adducts of 2, 9-dialkylpentacenes with diethyl azodicarboxylate
Okamoto K, et al.
Journal of Physical Organic Chemistry, 21(3), 257-262 (2008)
Enantioselective synthesis of aza-β-lactams via NHC-catalyzed [2+ 2] cycloaddition of ketenes with diazenedicarboxylates
Huang X-L, et al.
The Journal of Organic Chemistry, 74(19), 7585-7587 (2009)
The Mitsunobu reaction: origin, mechanism, improvements, and applications
But TYS and TPH
Chemistry - An Asian Journal, 2(11), 1340-1355 (2007)
DEAD-(cat) ZnBr2 an efficient system for the oxidation of alcohols to carbonyl compounds
Cao HT and Gree R
Tetrahedron Letters, 50(13), 1493-1494 (2009)
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