| Identification | Back Directory | [Name]
PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE | [CAS]
138687-69-1 | [Synonyms]
FDPP
Perfluorophenyl diphenylphosphinate
PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE
perfluorophenyl diphenylphosphinate(FDPP)
Diphenylphosphinic acid pentafluorophenyl ester
1-diphenylphosphoryloxy-2,3,4,5,6-pentafluorobenzene
Phosphinic acid, P,P-diphenyl-, 2,3,4,5,6-pentafluorophenyl ester | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C18H10F5O2P | [MDL Number]
MFCD00192380 | [MOL File]
138687-69-1.mol | [Molecular Weight]
384.24 |
| Chemical Properties | Back Directory | [Melting point ]
47-50 °C(lit.)
| [Boiling point ]
413.1±55.0 °C(Predicted) | [density ]
1.45 | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
solid | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C18H10F5O2P/c19-13-14(20)16(22)18(17(23)15(13)21)25-26(24,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H | [InChIKey]
OOWSDKUFKGVADH-UHFFFAOYSA-N | [SMILES]
P(C1=CC=CC=C1)(C1=CC=CC=C1)(OC1=C(F)C(F)=C(F)C(F)=C1F)=O |
| Hazard Information | Back Directory | [Chemical Properties]
White to yellow solid | [Uses]
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-L-valine thiazole amino acid to obtain its cyclic tetramers.
- Macrocyclization of an intermediate for the total synthesis of ziziphine N , and for the macrolactamization of precursor in synthesizing cryptophycin D.
| [Uses]
Pentafluorophenyl Diphenylphosphinate is a reagent used as carboxyl activating group and a coupling agent in variety of amide bond formations. | [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. |
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