10313. Propylphosphonic Anhydride

Nomenclature

CAS number: 68957-94-8
2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-trioxide; n-propane phosphonic acid anhydride; n-propylphosphonic cyclic anhydride; PPAA; T3P (Archimica).
C9H21O6P3; mol wt 318.18.
C 33.97%, H 6.65%, O 30.17%, P 29.20%.

Description and references

Coupling and water removal reagent often used in peptide synthesis. Prepn from n-propylphosphonic dichloride: H. Wissmann, H.-J. Kleiner, Angew. Chem. Int. Ed. Engl. 19, 133 (1980) DOI. Alternate synthetic method: M. Wehner et al., US 060264654 (2006). Synthetic applications: M. Ueda, T. Honma, Polym. J. 20, 477 (1988) DOI; K. S. Crichfield et al., Synth. Commun. 30, 3737 (2000) DOI; J. Hartund, M. Schwarz, Synlett 2000, 371 DOI. Reviews: M. Schwarz, ibid. 1369 DOI; A. L. L. García, ibid. 2007, 1328-1329 DOI.

Chemical structure

Properties

Colorless liquid, bp0.3 200°. Sol in ethyl acetate, dioxane, dichloromethane, THF, DMF.

Use

Reagent in synthetic organic chemistry.