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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

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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

Other Notes

Same product — same quality — now Sigma brand

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

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.




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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