11627

Diethyl azodicarboxylate solution

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

• 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

Properties

• grade: purum
• form: solid
• concentration: ~40% in toluene (H-NMR)
• refractive index: n20/D 1.47
• functional group: azo
• 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

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

Other Notes

Reagent used in the Mitsunobu reaction, reviews

Safety Information

• Pictograms: GHS02,GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H226,H304,H315,H319,H335,H336,H361d,H373,H412
• Precautionary Statements: P210 - P273 - P301 + P310 - P303 + P361 + P353 - P305 + P351 + P338 - P331
• 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
• 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