Di-Tert-Butyl Azodicarboxylate (CAS 870-50-8)

Physical Properties:

Appearance: Light yellow solid.

Molecular Formula: C10H18N2O4

Molecular Weight:26 g/mol.

Melting Point: 89–92 °C (literature).

Solubility: Soluble in organic solvents (e.g., MDC, ethyl acetate, methanol); insoluble in water.

Storage: Store refrigerated (2-8°C) and potentially under inert gas (like nitrogen).

Synonyms :

DBAD

Azodicarboxylic Acid Di-tert-butyl Ester

Di-tert-butyl Azodiformate

Bis(1,1-dimethylethyl)azodicarboxylate

Di-tert-butyl diazene-1,2-dicarboxylate

Key Uses

Electrophilic Amination: Introduces amino groups, particularly useful in synthesizing amino acid derivatives and other nitrogen-containing structures, often catalyzed by chiral organocatalysts.

Asymmetric Synthesis: Key in creating chiral molecules, including:

Asymmetric Michael additions.

Asymmetric Friedel-Crafts amination.

Synthesis of chiral hexapeptide fragments.

Peptide Synthesis: Used in creating complex peptide fragments and peptidomimetics.

• Mitsunobu Reactions: A reactant for preparing water-soluble prodrugs.
• Heterocycle Synthesis: Precursor for synthesizing dihydropyridazines and pyrroloisoquinolines.
• Dienophile: Reacts with dienes in Diels-Alder type reactions, forming dihydro derivatives.

Chemical Profile & Handling

• Synonyms: DBAD, Bis(1,1-dimethylethyl)azodicarboxylate, Di-tert-butyl azodiformate.
• Appearance: Yellow crystalline solid or powder.
• Storage: Sensitive to light and moisture; requires cool (2-8°C) and dark storage, often under an inert gas.
• Safety: Classified as flammable solid (H228) and irritant (H315, H319, H335).

Key Applications:

• Mitsunobu Reactions: Essential for coupling alcohols with acidic nucleophiles, forming new C-N, C-O, and C-S bonds.
• Asymmetric Synthesis: Used in chiral organocatalytic reactions, such as asymmetric Friedel-Crafts amination and Michael additions, to create specific stereoisomers.
• Peptide Synthesis: Key for preparing hexapeptide fragments and dipeptidyl peptidase IV prodrugs.
• Electrophilic Amination: Facilitates the addition of nitrogen to organic molecules, including beta-keto esters, often with chiral catalysts.
• API & Fine Chemical Manufacturing: Serves as a critical building block or catalyst in producing active pharmaceutical ingredients (APIs) and other specialty chemicals.
• Heterocycle Synthesis: Involved in creating complex ring structures like 3,6-dihydropyridazines.