What is Diphenylphosphoryl azide?

Identification

Product Name:    Diphenylphosphoryl azide    

Synonyms:    phosphorazidicacid,diphenylester;(PHO)2PO-N3;PHOSPHORIC ACID DIPHENYL ESTER AZIDE;PS-DPPA;Diphenylphosphorazindate（DPPA）;Diphenylphosphonicazide,97%;DPPA polymer-bound, PS-DPPA;DPPA, Phosphoric acid diphenyl ester azide    

CAS:    26386-88-9    

MF:    C12H10N3O3P    

MW:    275.2    

EINECS:    247-644-0

Properties

Boiling point     157 °C0.17 mm Hg(lit.)   

Density     1.277 g/mL at 25 °C(lit.)   

Refractive index     n20/D 1.551(lit.)   

Fp     >230 °F   

Storage temp.     2-8°C 

Form     Liquid    

Specific Gravity    1.277    

Color     slightly yellow   

Water Solubility     insoluble

Application

Diphenylphosphonic azide acts as a reagent for the synthesis of peptides and phosphoramidates by reacting with amines. It is also used in the preparation of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtis rearrangement. It is involved in pseudohalogen replacement of the azido group by treatment with nucleophilic reagents, such as water, butanol, ammonia, and various amines. Further, it is used as a hydroazidation catalyst for preparation of organoazides.

Diphenyl phosphoryl azide is used in the aziridination of olefins catalyzed by colbalt-tetraphenylporphyrin. It is also used as the activating agent in the preparation of macrocyclic lactams and of an aldose reductase inhibitor.

Instances

Phosphoryl Azide for Nosylation via Azidation

Phosphoryl Azide for Azidations

Condensing Agent

Experimental procedure): To an ice-cooled mixture containing 1 (2.5 mmol) and 2 (2.5 mmol) in dry DMF (15 mL), DPPA (3.0 mmol) is slowly added, followed by drop-wise addition of Et3N (6.3 mmol). The reaction mixture is kept at 0 °C for another 2 h, and then allowed to warm up to room temperature. After 24 h, the reaction mixture is diluted with EtOAc (80 mL) and washed with an aqueous solution of citric acid (10%, 50 mL), H2O (50 mL), saturated aqueous NaHCO3 (50 mL), H2O (50 mL), and brine (50 mL). The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue is purified by column chromatography to afford 3 (83% yield).