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Merck
CN

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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Product Name

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

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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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.

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.

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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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)
Polymer-supported triphenylphosphine: application in organic synthesis and organometallic reactions
Royal Society of Chemistry Advances, 9 (2019)
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)
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