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/REAXYS Number:
1911434
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

98%

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

89-92 °C (lit.)

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

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
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.

Packaging

5, 25 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Chirally aminated 2-naphthols--organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel-Crafts amination.
Sebastian Brandes et al.
Angewandte Chemie (International ed. in English), 45(7), 1147-1151 (2006-01-04)
Synlett, 2548-2548 (2006)
Masahiro Terada et al.
Journal of the American Chemical Society, 128(50), 16044-16045 (2006-12-15)
A newly designed axially chiral guanidine is found to function as an effective platform for asymmetric induction at the alpha-carbon of unsymmetrically substituted 1,3-dicarbonyl compounds. Highly efficient and enantioselective electrophilic amination of various 1,3-dicarbonyl compounds with azodicarboxylate was successfully achieved...
Articles
One of the most powerful and widely used carboncarbon bond forming reactions in organic synthesis is the Mitsunobu reaction.
Read More

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