Propanephosphonic acid anhydride

Propanephosphonic acid anhydride (PPAA, T3P) is an anhydride of propanephosphonic acid. Its structure is a cyclic trimer, with a phosphorus–oxygen core and propyl groups and additional oxygens attached.[1] The chemical is a useful reagent for peptide synthesis reactions, where it activates the carboxylic acid partner for subsequent reaction with amines. It is commercially available as 50 % solution in DMF or ethyl acetate as a slightly yellow mixture.

Propanephosphonic acid anhydride
Names
Preferred IUPAC name
2,4,6-Tripropyl-1,3,5,2λ5,4λ5,6λ5-trioxatriphosphinane-2,4,6-trione
Other names
PPACA; PPAA; T3P; Propylphosphonic anhydride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.102.078
EC Number
  • 422-210-5
UNII
  • InChI=1S/C9H21O6P3/c1-4-7-16(10)13-17(11,8-5-2)15-18(12,14-16)9-6-3/h4-9H2,1-3H3
    Key: PAQZWJGSJMLPMG-UHFFFAOYSA-N
  • CCCP1(=O)OP(=O)(OP(=O)(O1)CCC)CCC
Properties
C9H21O6P3
Molar mass 318.182 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H290, H314
P234, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P390, P404, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. "Propanephosphonic acid anhydride". Sigma-Aldrich.


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