Synonym(s): Bis(1,1-dimethylethyl)azodicarboxylate; DBAD; Di-tert-butyl azodiformate; NSC 109889
Formula: (CH3)3COCON=NCOOC(CH3)3
Formula Weight: 230.26
CAS No.: 870-50-8
Purity: ≥98.0% (GC)
Application: Reactant for:
• Preparation of hexapeptide key fragments via stereoselective selenocyclization/oxidative deselenylation or hydrazination/cyclization reactions
• Asymmetric Michael addition reactions
• Preparation of dipeptidyl peptidase IV dependent water-soluble prodrugs via Mitsunobu reaction
• Synthesis of pyrroloisoquinoline template via stereoselective N-acyliminium-mediated cyclization and enolate amination for synthesis of peptidomimetic compounds
• Barbier-type propargylation reactions
• Synthesis of bacterial peptide deformylase (PDF) inhibitor fumimycin
• Asymmetric amination of glycine Schiff bases
Other Notes: Acid labile reagent for Mitsunobu reactions allowing facile isolation of products 8; Electrophilic amination and hydrazination of enolates and lithium alkyls9,10,11
Storage: 2-8°C
Beilstein Registry Number: 1911434
EC No.: 212-796-9
Melting Point: 89-92°C(lit.); 89-92°C
Empirical Formula (Hill Notation): O3Sc2