Diphenylphosphorazidate

• CAT Number: R021723
• CAS Number: 26386-88-9
• Molecular Formula: C12H10N3O3P
• Molecular Weight: 275.20
• Purity: ≥95%
• Synonyms: Azidodiphenoxyoxophosphorane; DPPA; Diphenyl Azidophosphate; Diphenyl Phosphorazide; Diphenylphosphoryl Azide; O,O-Diphenylphosphoryl Azide; Phosphoric Acid Diphenyl Ester Azide
• Storage: -20°C
• IUPAC Name: [azido(phenoxy)phosphoryl]oxybenzene
• InChI: InChI=1S/C12H10N3O3P/c13-14-15-19(16,17-11-7-3-1-4-8-11)18-12-9-5-2-6-10-12/h1-10H
• InChIKey: SORGEQQSQGNZFI-UHFFFAOYSA-N
• SMILES: C1=CC=C(C=C1)OP(=O)(N=[N+]=[N-])OC2=CC=CC=C2

Diphenylphosphorazidate (Cat No.: R021723) is an organophosphorus compound with the formula (C₆H₅O)₂P(O)N₃. It is a colorless to pale yellow liquid widely used in organic synthesis, particularly for introducing azide functionality or in peptide bond formation. DPPA plays a key role in the Curtius rearrangement, converting carboxylic acids to isocyanates, which are then used to synthesize amines, ureas, or carbamates. It is valued for its mild reaction conditions and efficiency, making it a versatile reagent in medicinal and heterocyclic chemistry.