11625

Di-tert-butyl azodicarboxylate

purum, ≥98.0% (GC)

• Synonym(s): Bis(1,1-dimethylethyl)azodicarboxylate, DBAD, Di-tert-butyl azodiformate, NSC 109889
• Linear Formula: (CH₃)₃COCON=NCOOC(CH₃)₃
• CAS Number: 870-50-8
• Molecular Weight: 230.26
• Beilstein: 1911434
• EC Number: 212-796-9
• MDL number: MFCD00015001
• UNSPSC Code: 12352108
• PubChem Substance ID: 329749512
• NACRES: NA.22

Properties

• grade: purum
• Quality Level: 200
• Assay: ≥98.0% (GC)
• form: solid
• mp: 89-92 °C (lit.); 89-92 °C
• functional group: azo
• storage temp.: 2-8°C
• SMILES string: CC(C)(C)OC(=O)\N=N\C(=O)OC(C)(C)C
• InChI: 1S/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3/b12-11+
• InChI key: QKSQWQOAUQFORH-VAWYXSNFSA-N

Description

General description

Di-tert-butyl azodicarboxylate is a an acid labile reagent for Mitsunobu reactions allowing facile isolation of products and for the electrophilic amination and hydrazination of enolates and lithium alkyls.

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves