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135992

Sigma-Aldrich

Di-tert-butyl azodicarboxylate

greener alternative

98%

Synonym(s):
NSC 109889, DBAD, Di-tert-butyl azodiformate, Bis(1,1-dimethylethyl)azodicarboxylate
Linear Formula:
(CH3)3COCON=NCOOC(CH3)3
CAS Number:
Molecular Weight:
230.26
Beilstein:
1911434
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

89-92 °C (lit.)

greener alternative category

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

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalysis.

Application

Utilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst.
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
Reagent employed in the electrophilic amination of ß-keto esters catalyzed by an axially chiral guanidine. Building block in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such a L-proline or (S)-2-pyrrolidinyl tetrazole.
Co-oxidant in copper-catalyzed greener oxidation of alcohols under aerobic conditions.

Modified Markó′s aerobic oxidation of alcohols under atmospheric pressure with air or molecular oxygen at room temperature

Packaging

5, 25 g in glass bottle

Storage Class Code

13 - Non 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

Certificate of Analysis

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Certificate of Origin

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