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418080

Sigma-Aldrich

Pentafluorophenyl diphenylphosphinate

Synonym(s):

FDPP, Diphenylphosphinic acid pentafluorophenyl ester

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1 G
$81.79
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About This Item

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

$81.79

List Price$86.10Save 5%
Only 11 left in stockDetails
Request a Bulk Order

form

solid

Quality Level

100

mp

47-50 °C (lit.)

functional group

fluoro

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

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. [1][2] FDPP can be prepared from diphenylphosphinic chloride and pentafluorophenol in the presence of imidazole.[2]

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.[2]
  • Preparation of macrocyclic peptide cyclotheonamide B as a thrombin inhibitor.[3]
  • Cyclooligomerization of N-methylated-L-valine thiazole amino acid to obtain its cyclic tetramers.[4]
  • Macrocyclization of an intermediate for the total synthesis of ziziphine N [5], and for the macrolactamization of precursor in synthesizing cryptophycin D.[6]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS8105
MKCD1296
MKCC3889
MKBW7753V
MKBW9437V

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Pentafluorophenyl Diphenylphosphinate (FDPP)
Leonard MS, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-8 (2001)
Pentafluorophenyl Diphenylphosphinate (FDPP).
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2002)
A new synthesis of cyclotheonamide B via guanidination of ornithine
Jingen, Deng and Yasumasa, Hamada and Takayuki, Shioiri
Tetrahedron Letters, 37(13), 2261-2264 (1996)
Synthesis of novel N-methylated thiazole-based cyclic octa-and dodecapeptides.
Dudin L, et al.
Tetrahedron, 61(5), 1257-1267 (2005)
Total synthesis of cryptophycins. Revision of the structures of cryptophycins A and C.
Barrow R A, et al.
Journal of the American Chemical Society, 117(9), 2479-2490 (1995)
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