11625
Di-tert-butyl azodicarboxylate
purum, ≥98.0% (GC)
Synonym(s):
Bis(1,1-dimethylethyl)azodicarboxylate, DBAD, Di-tert-butyl azodiformate, NSC 109889
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About This Item
Linear Formula:
(CH3)3COCON=NCOOC(CH3)3
CAS Number:
Molecular Weight:
230.26
Beilstein:
1911434
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
grade
purum
Quality Level
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
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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
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
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J.L. Vicario et al.
Tetrahedron Letters, 40, 7123 -7123 (1999)
D.A. Evans et al.
Journal of the American Chemical Society, 108, 6395-6395 (1986)
C. Gennari et al.
Journal of the American Chemical Society, 108, 6394-6394 (1986)
Masaru Kondo et al.
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
M. Kiankarimi et al.
Tetrahedron Letters, 40, 4497 -4497 (1999)
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