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93094

Sigma-Aldrich

Triphenylphosphine, polymer-bound

100-200 mesh, extent of labeling: ~1.6 mmol/g 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:
12352128
PubChem Substance ID:
57653516
NACRES:
NA.22

form

solid

Quality Level

100

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

~1.6 mmol/g loading

matrix

crosslinked with 1% DVB

particle size

100-200 mesh

functional group

phosphine

storage temp.

2-8°C

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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General description

Triphenylphosphine, polymer-bound is polystyrene crosslinked with divinylbenzene, widely used in many organic syntheses such as peptide synthesis, heterocycle synthesis, esterification, and total synthesis. It can be easily removed from the reaction products by simple filtration.

Application

Triphenylphosphine, polymer-bound is used as a polymer support to synthesize dipeptides, olefins, aryl-alkyl ethers, and in the esterification of alkylphosphonic acids. It acts as a Lewis acid, and dehydrating agent when complexed with halogen, hence useful in the acetonation of sugars.

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Polymer-bound triphenylphosphine as traceless reagent for Mitsunobu reactions in combinatorial chemistry: Synthesis of aryl ethers from phenols and alcohols
Tetrahedron Letters, 48, 8751-8754 (1998)
Mild and efficient esterification of alkylphosphonic acids using polymer-bound triphenylphosphine
Tetrahedron Letters, 53, 3795-3797 (2012)
Synthesis of aryl ethers from aminoalcohols using polymer-supported triphenylphosphine
Tetrahedron Letters, 43, 2157-2159 (2002)
Triphenylphosphine polymer-bound/iodine complex: A suitable reagent for the preparation of O-isopropylidene sugar derivatives
Synthesis, 2006, 305-308 (2006)
Polymer-supported triphenylphosphine: application in organic synthesis and organometallic reactions
Royal Society of Chemistry Advances, 9 (2019)
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