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Key Documents

135992

Sigma-Aldrich

Di-tert-butyl azodicarboxylate

greener alternative

98%

Sinonimo/i:

Bis(1,1-dimethylethyl)azodicarboxylate, DBAD, Di-tert-butyl azodiformate, NSC 109889

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About This Item

Formula condensata:
(CH3)3COCON=NCOOC(CH3)3
Numero CAS:
Peso molecolare:
230.26
Beilstein:
1911434
Numero CE:
Numero MDL:
Codice UNSPSC:
12352108
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

98%

Forma fisica

solid

Caratteristiche più verdi

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Punto di fusione

89-92 °C (lit.)

Categoria alternativa più verde

Temperatura di conservazione

2-8°C

Stringa SMILE

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+
QKSQWQOAUQFORH-VAWYXSNFSA-N

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Categorie correlate

Descrizione generale

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)

Applicazioni

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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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
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)

Articoli

Reagents for the Mitsunobu Reaction

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