135992
Di-tert-butyl azodicarboxylate
98%
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:
Molecular Weight:
230.26
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-796-9
Beilstein/REAXYS Number:
1911434
MDL number:
Assay:
98%
Form:
solid
Quality Level
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.)
functional group
azo
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
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)
Automate your Mitsunobu reactions with Synple Automated Synthesis Platform (SYNPLE-SC002)
Application
Reagent employed in the electrophilic amination of β-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
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
Utilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 135992-25G | 04061838731074 |
| 135992-5G | 04061838731081 |