Di-tert-butyl azodicarboxylate, 98%

Description

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.

Specifications

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

• Melting Point: 89°C to 92°C
• Quantity: 5 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

Safety and Handling

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

SDS

RUO – Research Use Only