7-Azabenzotriazol-1-yloxytris(dimethyla-mino)phosphonium Hexafluorophosphate

Abstract

[156311-85-2] C11H21F6N7OP2 (MW 443.27) InChI = 1S/C11H21N7OP.F6P/c1-15(2)20(16(3)4,17(5)6)19-18-11-10(13-14-18)8-7-9-12-11;1-7(2,3,4,5)6/h7-9H,1-6H3;/q+1;-1 InChIKey = RQBNNDQCKMIUQJ-UHFFFAOYSA-N (peptide coupling agent) Alternate Name: AOP. Solubility: soluble in N,N-dimethylformamide. Form Supplied in: not commercially available. Preparative Methods: AOP is prepared by reaction of 2-chloro-tri(dimethylamino)phosphonium chloride with 1-hydroxy-7-azabenzotriazole (HOAt) to give 7-azabenzotriazol-1-yloxytris(dimethylamino)phosphonium chloride. The chloride is then exchanged with KPF6 to give AOP in a way similar to that used for the preparation of benzotriazol-1-yloxytris(dimethylam-ino)phosphonium hexafluorophosphate (BOP).1 Handling, Storage, and Precautions: follow general recommendations for uronium/aminium type of reagents such as BOP or N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosp-hate N-oxide (HATU). A main by-product of AOP reaction is carcinogenic HMPA, and therefore the reagent must be handled with caution in a fume hood.2