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93093

Sigma-Aldrich

Triphenylphosphine, polymer-bound

100-200 mesh, extent of labeling: ~3 mmol/g triphenylphosphine loading

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Synonym(s):
Copolymer of styrene and divinylbenzene, diphenylphosphinated, Diphenylphosphino-polystyrene, Polystyrene crosslinked with divinylbenzene, diphenylphosphinated
Linear Formula:
-C6H4P(C6H5)2
CAS Number:
39319-11-4
Molecular Weight:
262.29
MDL number:
MFCD00148025
UNSPSC Code:
12352200
PubChem Substance ID:
57653515
NACRES:
NA.22

form

solid

Quality Level

200

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reaction type: solution phase peptide synthesis
reagent type: ligand

extent of labeling

~3 mmol/g triphenylphosphine loading

matrix

crosslinked with 2% DVB

particle size

100-200 mesh

functional group

phosphine oxide

SMILES string

c1ccc(cc1)P(c2ccccc2)c3ccccc3

InChI

1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

InChI key

RIOQSEWOXXDEQQ-UHFFFAOYSA-N

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Application

Polymer-bound triphenylphosphine is a solid-supported reagent that can be used as a better alternative to triphenylphosphine in the Mitsunobu reaction.
It can also be used:
  • For the esterification of alkylphosphonic acids using primary alcohols in the presence of iodine and imidazole.
  • To catalyze the conversion of 3-[3-(1,3-dioxolan-2-yl)-1-hydroxypropyl]pyridine to 3-[1-bromo-3-(1,3-dioxolan-2-yl)propyl]pyridine using carbon tetrabromide.
  • To isomerize (Z)-nitro olefins to the (E)-isomers.
  • To prepare polymer-bound ylides which are useful in Wittig reactions.
  • To convert alcohols or carboxylic acids to the corresponding chlorides.
  • In combination with carbon tetrachloride for the coupling N-alkoxycarbonyl α-amino acids and primary amines to form the corresponding amides.

Other Notes

Polymer-bound triphenylphosphine is used for preparing polymer-bound yields which are highly useful for Wittig reactions; removal of the polymer at the end of the reaction removes all the phosphine oxide.

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The use of polymer-bound triphenylphosphine and carbon tetrachloride for condensation of N-alkoxycarbonyl α-amino acids and primary amines.
Landi Jr J J and Brinkman H R
Synthesis, 1992(11), 1093-1095 (1992)
Synthesis of nornicotine, nicotine and other functionalised derivatives using solid-supported reagents and scavengers.
Baxendale I R, et al.
Journal of the Chemical Society. Perkin Transactions 1, 2, 143-154 (2002)
Synthesis of (E)-nitro olefins by isomerisation of (Z)-nitro olefins with polymer-supported triphenylphosphine.
Stanetty P and Kremslehner M
Tetrahedron Letters, 39(8), 811-812 (1998)
The Use of Polymer-Bound Triphenylphosphine in the Stereochemical Inversion of Secondary Alcohols.
White J M, et al.
Combinatorial Chemistry & High Throughput Screening, 3(2), 103-106 (2000)
M. Bernard et al.
The Journal of Organic Chemistry, 48, 3164-3164 (1983)
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