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11625 Sigma

Di-tert-butyl azodicarboxylate

purum, ≥98.0% (GC)

Synonym: Bis(1,1-dimethylethyl)azodicarboxylate, DBAD, Di-tert-butyl azodiformate, NSC 109889

  • CAS Number 870-50-8

  • Linear Formula (CH3)3COCON=NCOOC(CH3)3

  • Molecular Weight 230.26

  •  Beilstein Registry Number 1911434

  •  EC Number 212-796-9

  •  MDL number MFCD00015001

  •  PubChem Substance ID 329749512

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Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Synthesis, Mitsunobu, Synthetic Reagents
InChI Key   QKSQWQOAUQFORH-VAWYXSNFSA-N
grade   purum
assay   ≥98.0% (GC)
mp   89-92 °C(lit.)
  89-92 °C
storage temp.   2-8°C

Description

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

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.

Price and Availability


Laboratory Gloves

Cross-Coupling Guide
Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

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