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

CAS Number

* 68957-94-8

3D model (JSmol)

* Interactive image

ChemSpider |

* 100355

EC Number |

* 422-210-5

PubChem CID

* 111923

UNII |

* I6EGD8839N

InChI

* 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

SMILES

* CCCP1(=O)OP(=O)(OP(=O)(O1)CCC)CCC

Properties

Chemical formula

| C9H21O6P3
Molar mass | 318.182 g·mol−1
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H290, H314

GHS precautionary statements

| P234, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, 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

Propanephosphonic acid anhydride (PPAA, T3P) is the trimeric anhydride of n-propylphosphonic acid. It is a useful reagent for peptide synthesis reactions, where it activates the carboxylic acid partner for subsequent reaction with a primary or secondary amine. It is commercially available as 50 % solution in DMF or ethyl acetate as a slightly yellow mixture. [1][2]

## References

1. ↑ Dunetz, Joshua R.; Magano, Javier; Weisenburger, Gerald A. (2016-02-19). "Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals". Organic Process Research & Development 20 (2): 140–177. doi:10.1021/op500305s. ISSN 1083-6160. https://pubs.acs.org/doi/10.1021/op500305s. Retrieved 2025-07-26.
2. ↑ "Propanephosphonic acid anhydride". Sigma-Aldrich. https://www.sigmaaldrich.com/catalog/product/mm/843943.

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*[CID]: Compound ID
*[H290]: May be corrosive to metals
*[H314]: Causes severe skin burns and eye damage
*[P234]: Keep only in original container
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P321]: Specific treatment (see … on this label)
*[P363]: Wash contaminated clothing before reuse
*[P390]: Absorb spillage to prevent material damage
*[P404]: Store in a closed container
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …