diphenyl phosphoryl azide, CAS No. 26386-88-9

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26386-88-9

Catalog No. EBD42812

CAS 26386-88-9

Name diphenyl phosphoryl azide

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Basic Information

Synonyms: diphenylazidophosphate Diphenylphosphorylazide diphenylphosphorazidate DIPHENYLPHOSPHORYLAZIDE,POLYMER-BOUND DIPHENYLPHOSPHORICAZIDE DIPHENYLPHOSPHONICAZIDE DPPAPOLYMER-BOUND diphenylphosphinicazide

Molecular Formula: C12H10N3O3P

Molecular Weight: 275.2

MDL Number: MFCD00001987

Categories: Synthetic Chemistry > Organic Building Blocks > Special Functional Group Blocks

Product Description:

Diphenyl phosphoryl azide (DPPA, CAS 26386-88-9) is a versatile organic reagent featuring a phosphoryl azide functional group. It is a colorless to pale yellow liquid, widely used in organic synthesis for its unique reactivity. Structurally, it combines a diphenyl phosphate moiety with an azide group, enabling both nucleophilic and electrophilic transformations. DPPA is primarily employed as a coupling reagent in peptide synthesis, facilitating the formation of amide bonds from carboxylic acids and amines under mild conditions. It also serves as a key reagent for the Curtius rearrangement, converting carboxylic acids into isocyanates, which can be further transformed into amines, carbamates, or ureas. Additionally, DPPA acts as an azide transfer agent, introducing azide groups into organic molecules for click chemistry or further functionalization. Its applications extend to the synthesis of heterocycles, pharmaceuticals, and natural products. Due to its high reactivity and thermal sensitivity, DPPA should be handled with care, avoiding exposure to heat, shock, or strong acids. It is a standard tool in both academic and industrial research laboratories, particularly in medicinal chemistry and drug discovery.

Physical Properties

Boiling Point: 157 °C/0.17 mmHg(lit.)

Flash Point: 112 °C

Density: 1.277 g/mL at 25 °C(lit.)

Solubility: insoluble

Refractivity: n20/D 1.551(lit.)

Storage: 2-8°C

Safety Information

Packing Level: II

Hazard Category: 6.1

Transport Codes: 3278

Analytical Data

Appearance: colourless or faintly yellow liquid