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11625

Sigma-Aldrich

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:
870-50-8
Molecular Weight:
230.26
Beilstein/REAXYS Number:
1911434
EC Number:
212-796-9
MDL number:
MFCD00015001
UNSPSC Code:
12352108
PubChem Substance ID:
329749512
NACRES:
NA.22

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

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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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C. Gennari et al.
Journal of the American Chemical Society, 108, 6394-6394 (1986)
Cong-Bin Ji et al.
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.
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)
M. Kiankarimi et al.
Tetrahedron Letters, 40, 4497-4497 (1999)
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