Pentafluorophenyl diphenylphosphinate
ALDRICH/418080
Synonym: FDPP; Diphenylphosphinic acid pentafluorophenyl ester
CAS Number: 138687-69-1
Empirical Formula (Hill Notation): C18H10F5O2P
Molecular Weight: 384.24
MDL Number: MFCD00192380
Linear Formula: (C6H5)2P(O)OC6F5
Product Type: Chemical
| form | solid |
| InChI | 1S/C18H10F5O2P/c19-13-14( |
| InChI key | OOWSDKUFKGVADH-UHFFFAOYSA |
| mp | 47-50 °C (lit.) |
| SMILES string | Fc1c(F)c(F)c(OP(=O)(c2ccc |
| Application: | Catalyst involved in coupling and macrocyclization Reagent used in: • Fmoc solid-phase synthesis • Synthesis of phorboxazoles, furan-based cyclic homoligopeptides, and ziziphine N |
| Application: | FDPP can be used as a coupling reagent in the: • Synthesis of peptides by solid-phase and solution-phase reactions. • Preparation of macrocyclic peptide cyclotheonamide B as a thrombin inhibitor. • Cyclooligomerization of N-methylated- • Macrocyclization of an intermediate for the total synthesis of ziziphine N , and for the macrolactamization of precursor in synthesizing cryptophycin D. |
| General description: | Pentafluorophenyl diphenylphosphinate (FDPP) is a reagent, used as a coupling agent in the amide bond forming reactions without racemization. It can also be employed in the synthesis of dipeptides with high yields and good optical purity. FDPP can be prepared from diphenylphosphinic chloride and pentafluorophenol in the presence of imidazole. |
| Packaging: | 1, 5 g in glass bottle |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| mp | 47-50 °C (lit.) |
| UNSPSC | 12352101 |