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11627 Aldrich

Diethyl azodicarboxylate solution

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

Synonym: 1,2-Ethoxycarbonyl diazene solution, DEAD, Diethoxycarbonyldiazene solution, Diethyl azodiformate solution, NSC 3474, NSC 679015, Unifoam AZ-AE 200

  • CAS Number 1972-28-7

  • Linear Formula C2H5OCON=NCOOC2H5

  • Molecular Weight 174.15

  •  Beilstein Registry Number 908662

  •  MDL number MFCD00009103

  •  PubChem Substance ID 57646942

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Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Synthesis, Mitsunobu, Synthetic Reagents
InChI Key   FAMRKDQNMBBFBR-BQYQJAHWSA-N
grade   purum
concentration   ~40% in toluene (H-NMR)
refractive index   n20/D 1.47
storage temp.   2-8°C

Description

Other Notes

Reagent used in the Mitsunobu reaction, reviews

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

Price and Availability

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
RIDADR 
UN3379 - DOT UN3223 class 3 - PG 1 - Desensitized explosive, liquid, n.o.s. (Diethyl Azodicarboxylate 40% solution in toluene);Hi:ALL
WGK Germany 
3
Flash Point(F) 
105.8 °F
Flash Point(C) 
41 °C

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

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