Dibenzyl Phosphorochloridate

[538-37-4] C14H14ClO3P (MW 296.69) InChI = 1S/C14H14ClO3P/c15-19(16,17-11-13-7-3-1-4-8-13)18-12-14-9-5-2-6-10-14/h1-10H,11-12H2 InChIKey = YADJFRGSGWGMNH-UHFFFAOYSA-N (phosphorylating reagent for alcohols,2 phenols,3 amines,4 and amides;5 removal of benzyl groups from the products affords phosphoric monoesters and monoamides respectively) Alternate Name: BPC. Physical Data: undistillable thick oil. Analysis of Reagent Purity: NMR: δP +4.7, +3.5 ppm. Preparative Methods: oxidative halogenation of dibenzyl phosphite using Cl2 or N-chlorosuccinimide6 yields dibenzyl phosphorochloridate (BPC). The reaction of dibenzyl hydrogen phosphate with PCl5 is also used.7 The latter procedure is employed for the preparation of p-substituted benzyl derivatives such as p-nitrobenzyl8 and p-chlorobenzyl.9 These substituted benzyl phosphates are crystalline and more stable than BPC but have reactivities similar to the parent chloridate. Handling, Storage, and Precautions: dibenzyl phosphorochloridate may be stored in the cold but preferably prepared just prior to use. Distillation of the chloridate may cause violent decomposition.