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Di-tert-butyl azodicarboxylate, 98%

Catalog No. aal0029414
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25 g
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Catalog No. AAL0029414 Supplier Thermo Scientific Chemicals Supplier No. L0029414
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CAS: 870-50-8 | C10H18N2O4 | 230.264 g/mol

Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions.

Solubility
Soluble in most organic solvents. Insoluble in water.

Notes
Light sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong bases and alcohols.

Chemical Identifiers

CAS 870-50-8
Molecular Formula C10H18N2O4
Molecular Weight (g/mol) 230.264
MDL Number MFCD00015001
InChI Key QKSQWQOAUQFORH-VAWYXSNFSA-N
Synonym di-tert-butyl azodicarboxylate, di-tert-butylazodicarboxylate, di-tert-butyl diazene-1,2-dicarboxylate, azodicarboxylic acid di-tert-butyl ester, di-tert-butyl azodicarboxylate dbad, pubchem17548, n-tert-butoxycarbonyl imino tert-butoxy formamide, tert-butyl tert-butyl oxycarbonyl diazenyl formate, n-tert-butoxy carbonyl imino tert-butoxy formamide, 1,2-diazenedicarboxylic acid, 1,2-bis 1,1-dimethylethyl ester
PubChem CID 6034084
IUPAC Name tert-butyl (NE)-N-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate
SMILES CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C

Specifications

Melting Point 89°C to 92°C
Quantity 25 g
Beilstein 1911434
Sensitivity Light sensitive
Solubility Information Soluble in most organic solvents. Insoluble in water.
Formula Weight 230.27
Percent Purity 98%
Chemical Name or Material Di-tert-butyl azodicarboxylate
Hazard Category H228-H315-H319-H335
Hazard Statement GHS H Statement
H315-H319-H335
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary Statement P210-P240-P241-P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P370+P378q-P501c
DOTInformation Hazard Class: 4.1; Packaging Group: III
EINECSNumber 212-796-9
TSCA No
Recommended Storage Ambient temperatures

RUO – Research Use Only