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Sigma-Aldrich

Di-tert-butyl azodicarboxylate

greener alternative

98%

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Synonym(s):
Bis(1,1-dimethylethyl)azodicarboxylate, DBAD, Di-tert-butyl azodiformate, NSC 109889
Linear Formula:
(CH3)3COCON=NCOOC(CH3)3
CAS Number:
870-50-8
Molecular Weight:
230.26
Beilstein:
1911434
EC Number:
212-796-9
MDL number:
MFCD00015001
UNSPSC Code:
12352108
PubChem Substance ID:
24848251
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

89-92 °C (lit.)

greener alternative category

Aligned,

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.

Automate your Mitsunobu reactions with Synple Automated Synthesis Platform (SYNPLE-SC002)

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
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.
Utilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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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)
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
Synlett, 2548-2548 (2006)

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