Diphenyl Phophoryl Azide(DPPA) (CAS 26386-88-9)

Storage & Handling:

• Store refrigerated (2-8°C).
• Store under an inert gas (like Nitrogen or Argon).
• Incompatible with acids and strong oxidizing agents.

Uses

• Peptide Synthesis: Diphenyl Phophoryl Azide(DPPA) (CAS 26386-88-9), Connects amino acids and peptides efficiently, preventing racemization (loss of stereochemistry).
• Curtius Rearrangement: Converts carboxylic acids into amines, carbamates, or isocyanates under mild conditions, avoiding hazardous intermediates.
• Azide Introduction: Acts as a source of the azide group

for synthesizing organoazides and in click chemistry.

• Pharmaceuticals: Used in developing drugs, including inhibitors for aldose reductase, and creating complex organic molecules.
• Biomaterial Crosslinking: Helps crosslink collagen to improve its resistance to degradation in the body.

Reactions & Transformations:

• Forms amides/urethanes from carboxylic acids and amines.
• Enables stereospecific azide formation from alcohols.
• Catalyzes cobalt-mediated aziridination of olefins.
• Used in Mitsunobu inversions and preparing acyl azides.

Characteristics:

• A toxic, potentially explosive chemical, requiring careful handling (store cool, under inert gas, away from moisture).

Other Uses:

• Aziridination of olefins.
• Preparation of amino acid copolymers

Key Applications

• Azide Introduction: Acts as a hydroazidation catalyst for organoazide synthesis.
• Peptide Synthesis: Used in peptide coupling reactions and forming amide/urethane linkages.
• Complex Molecule Synthesis: Essential for creating oligosaccharides with carbamate/urea bonds, aldose reductase inhibitors, and other complex pharmaceuticals.
• Click Chemistry: A key reagent for azidation and diazo transfer reactions, enabling efficient C-N bond formation.
• Macrocyclic Lactams: Functions as an activating agent for preparing large ring structures.

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