T3P activates carboxylic acids toward nucleophilic attack by amines, forming amide bonds with minimal racemization at stereocenters. Its water-soluble phosphonate by-products simplify aqueous workup compared to classical carbodiimide-based coupling reagents, and it is widely adopted in industrial-scale API amide-coupling processes, including for peptide and small-molecule pharmaceutical synthesis.
T3P (propanephosphonic acid anhydride) is a cyclic trimeric phosphonic anhydride widely used as a low-toxicity, low-epimerization coupling reagent for amide and peptide bond formation, valued for its water-soluble by-products and broad functional-group tolerance.
| Chemical Name | Propanephosphonic Acid Anhydride (T3P; n-Propylphosphonic Anhydride) |
| CAS Number | 68957-94-8 |
| IUPAC Name | 2,4,6-Tripropyl-1,3,5,2?5,4?5,6?5-trioxatriphosphinane-2,4,6-trione |
| Molecular Formula | C9H21O6P3 |
| Molecular Weight | 318.18 g/mol g/mol |
| Boiling Point | 200°C at 0.3 torr |
| Density | 1.069 g/mL at 25°C |
| Refractive Index | 1.418 |
Low-epimerization coupling reagent for solution-phase and solid-phase peptide synthesis.
Widely used in industrial process chemistry for amide coupling steps in small-molecule drug synthesis.
Preferred over classical carbodiimide reagents for its water-soluble, easily removed by-products.
Used in ester synthesis, Weinreb amide formation, and various dehydration/cyclization reactions.
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