418080

Pentafluorophenyl diphenylphosphinate

• Synonym(s): FDPP, Diphenylphosphinic acid pentafluorophenyl ester
• Linear Formula: (C₆H₅)₂P(O)OC₆F₅
• CAS Number: 138687-69-1
• Molecular Weight: 384.24
• MDL number: MFCD00192380
• UNSPSC Code: 12352101
• PubChem Substance ID: 24866201
• NACRES: NA.22

Properties

• form: solid
• Quality Level: 100
• mp: 47-50 °C (lit.)
• SMILES string: Fc1c(F)c(F)c(OP(=O)(c2ccccc2)c3ccccc3)c(F)c1F
• 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
• InChI key: OOWSDKUFKGVADH-UHFFFAOYSA-N

Description

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.

Application

Catalyst involved in coupling and macrocyclization

Reagent used in:

• Fmoc solid-phase synthesis
• Synthesis of phorboxazoles, furan-based cyclic homoligopeptides, and ziziphine N

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves