Oxobis[tris Dimethylamino Phosphonium] Bis(Tetrafluoroborate)

Abstract

[55881‐03‐3] C12H36B2F8N6OP2 (MW 516.10)

InChI = 1S/C12H36N6OP2.2BF4/c1‐13(2)20(14(3)4,15(5)6)19‐21(16(7)8,17(9)10)18(11)12;2*2‐1(3,4)5/h1‐12H3;;/q+2;2*‐1

InChIKey = MSSSPRSPUHPRKJ‐UHFFFAOYSA‐N

(a mild dehydrating agent, useful in peptide synthesis,2 dehydration of aldoximes to nitriles3 and Beckmann or Lossen‐type rearangements3)

Alternate Name: Bates’ reagent.

Physical Data: mp 194–204 °C.

Solubility: insol ether, EtOAc, THF, CH2Cl2, CHCl3; sol MeCN, DMF, HMPA.

Form Supplied in: white crystalline solid; limited commercial availability.

Preparative Methods: by treatment of Hexamethylphosphoric Triamide with p‐toluenesulfonic anhydride at 55 °C for 3 h, isolation of the bis(p‐toluenesulfonate), then treatment with NaBF4 in MeCN.2

Handling, Storage, and Precautions: can be used with care without special precautions; however, it reacts with water to produce HMPA (carcinogenic) and HBF4 (corrosive).