DPPA

(Diphenylphosphoryl Azide)

Other Names:

Diphenyl phosphorazidate

Phosphoric acid diphenyl ester azide

General Information:

Structure:

CAS Number: 26386-88-9

Molecular Weight: 275.20 g/mol

Appearance: Colorless to light yellow liquid

Boiling Point: 157 C

Density: 1.277 g/mL

Common Uses:

Reagent in Mitsunobu reactions for the formation of azide products

Procedure excerpt:

To a solution of the SM (3.1 g, 16.2 mmol) in THF (60 mL) at 0 C was added DIAD (6.3 mL, 32.0 mmol), PPh3 (8.52 g, 32.5 mmol), and DPPA (6.98 mL, 32.5 mmol). The reaction . . .

[full procedure]

Reagent for the conversion of alcohols to azides (DPPA + DBU)

Procedure excerpt:

To a suspension of the SM (0.665 g, 1.66 mmol) in THF (10 mL) at RT under Ar was added DPPA (0.400 mL, 1.83 mmol) and DBU (0.297 mL, 1.99 mmol). The resulting mixture . . .

[full procedure]

Safety:

Diphenylphosphoryl azide (DPPA) is toxic and an irritant. DPPA decomposes at >200 C.

References:

1) Patent Reference: WO2007117607, page 312, (12.9 MB)

2) Patent Reference: WO2015144799, page 343, (18.8 MB)

3) Pearson, A. J.; Roush, W. R.; Handbook of Reagents for Organic Synthesis, Activating Agents and Protecting Groups

4) Wikipedia: Diphenylphosphoryl azide (link)

5) www.sigmaaldrich.com: Diphenyl phosphoryl azide (link)