11625
Di-tert-butyl azodicarboxylate
purum, ≥98.0% (GC)
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Bis(1,1-dimethylethyl)azodicarboxylate, DBAD, Di-tert-butyl azodiformate, NSC 109889
(CH3)3COCON=NCOOC(CH3)3
Recommended Products
grade
purum
Quality Level
Assay
≥98.0% (GC)
form
solid
mp
89-92 °C (lit.)
89-92 °C
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
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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
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Angewandte Chemie (International ed. in English), 54(28), 8198-8202 (2015-05-28)
The catalytic enantioselective reaction of diphenylmethylidene-protected α-aminoacetonitriles with imines has been developed. Good yields and diastereo- and enantioselectivities were observed for the reaction of various imines using chiral bis(imidazoline)/Pd catalysts. The reaction of α-aminonitriles with di-tert-butyl azodicarboxylate afforded chiral α,α-diaminonitriles
Tetrahedron Letters, 40, 7123 -7123 (1999)
Journal of the American Chemical Society, 108, 6395-6395 (1986)
Organic & biomolecular chemistry, 10(6), 1158-1161 (2012-01-11)
We report the first example of catalytic asymmetric direct amination of α-monosubstituted nitroacetates using di-tert-butyl azodicarboxylate. The simple and easily available Hatakeyama's catalyst β-ICD 11 was found to be a highly enantioselective catalyst for this reaction.
Journal of the American Chemical Society, 108, 6394-6394 (1986)
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