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Merck

93094

Triphenylphosphine, polymer-bound

100-200 mesh, extent of labeling: ~1-1.5 mmol/g Capacity (Phosphor)

Synonym(s):

Copolymer of styrene and divinylbenzene, diphenylphosphinated, Diphenylphosphino-polystyrene, Polystyrene crosslinked with divinylbenzene, diphenylphosphinated

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About This Item

Linear Formula:
-C6H4P(C6H5)2
CAS Number:
39319-11-4
Molecular Weight:
262.29
NACRES:
NA.22
PubChem Substance ID:
57653516
UNSPSC Code:
12352128
MDL number:
MFCD00148025

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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

SMILES string

c1ccc(cc1)P(c2ccccc2)c3ccccc3

InChI key

RIOQSEWOXXDEQQ-UHFFFAOYSA-N

form

solid

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

~1-1.5 mmol/g Capacity (Phosphor)

matrix

crosslinked with 1% DVB

particle size

100-200 mesh

functional group

phosphine

storage temp.

2-8°C

Quality Level

100

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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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6830
BCCM4698
BCCL8291
BCCL1586
BCCK3042

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Synthesis of aryl ethers from aminoalcohols using polymer-supported triphenylphosphine
Tetrahedron Letters, 43, 2157-2159 (2002)
Mild and efficient esterification of alkylphosphonic acids using polymer-bound triphenylphosphine
Tetrahedron Letters, 53, 3795-3797 (2012)
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)
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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