Diphenyl Phosphorazidate

[26386-88-9] C12H10N3O3P (MW 275.22) 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 (peptide synthesis;1 synthesis of α-aryl carboxylic acids;4 synthesis of thiol esters;7, 8 stereospecific conversion of alcohols to azides;9 ring contraction of cycloalkanones;13 decarbonylation of aldehydes26) Alternate Names: DPPA; O,O-diphenylphosphoryl azide. Physical Data: bp 157 °C/0.17 mmHg; d 1.277 g cm−3; fp >110 °C. Solubility: sol toluene, THF, DMF, tert-butyl alcohol. Form Supplied in: colorless liquid; commercially available in kilogram quantities. Preparative Methods: by the reaction of Diphenyl Phosphorochloridate with a slight excess of Sodium Azide in acetone at rt (85–90% yield).1 Purification: vacuum distillation (bath temp <200 °C, dec >200 °C). Handling, Storage, and Precautions: handle and store under nitrogen. Refrigerate. Decomposes at >200 °C and may produce toxic fumes of phosphorus oxides and/or phosphine. Toxic, irritant. Harmful if swallowed, inhaled, or absorbed through the skin. Use in fume hood. Incompatible with oxidizing agents and acids. Hazardous combustion or decomposition products include carbon monoxide, carbon dioxide, and nitrogen oxides. Prolonged contact with moisture may produce explosive hydrogen azide (HN3).