11627

Diethyl azodicarboxylate solution

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

• Synonyme(s) : 1,2-Ethoxycarbonyl diazene solution, DEAD, Diethoxycarbonyldiazene solution, Diethyl azodiformate solution, NSC 3474, NSC 679015, Unifoam AZ-AE 200
• Formule linéaire : C₂H₅OCON=NCOOC₂H₅
• Numéro CAS: 1972-28-7
• Poids moléculaire : 174.15
• Numéro Beilstein : 908662
• Numéro MDL: MFCD00009103
• Code UNSPSC : 12352108
• ID de substance PubChem : 57646942
• Nomenclature NACRES : NA.22

Propriétés

• Qualité: purum
• Niveau de qualité: 100
• Forme: solid
• Concentration: ~40% in toluene (H-NMR)
• Indice de réfraction: n20/D 1.47
• Groupe fonctionnel: azo
• Température de stockage: 2-8°C
• Chaîne SMILES: 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+
• Clé InChI: FAMRKDQNMBBFBR-BQYQJAHWSA-N

Description

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

Autres remarques

Reagent used in the Mitsunobu reaction, reviews

Informations sur la sécurité

• Pictogrammes: GHS02,GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H226,H304,H315,H319,H335,H336,H361d,H373,H412
• Conseils de prudence: P210 - P273 - P301 + P310 - P303 + P361 + P353 - P305 + P351 + P338 - P331
• Classification des risques: Aquatic Chronic 3 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3
• Organes cibles: Central nervous system, Respiratory system
• Code de la classe de stockage: 3 - Flammable liquids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 105.8 °F - closed cup
• Point d'éclair (°C): 41 °C - closed cup
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter