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563110

Sigma-Aldrich

Diethyl azodicarboxylate solution

40 wt. % in toluene

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:
Molecular Weight:
174.15
Beilstein:
908662
MDL number:
PubChem Substance ID:

Quality Level

concentration

40 wt. % in toluene

refractive index

n20/D 1.4690

bp

116-117 °C

density

0.956 g/mL at 25 °C

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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General description

DOT Special Approval Submission is Under Review. Availability is Estimated as March 2012.

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
A commonly used activating reagent in Mitsunobo reactions.

Packaging

25, 100 g in glass bottle
100g unit contains ca. 40g DEAD solute
25g unit contains ca. 10g DEAD solute

Warning

Toxic, Irritant, Flammable

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

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

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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