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93093

Triphenylphosphine, polymer-bound

Name: Triphenylphosphine, polymer-bound
Brand: ALDRICH

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

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:

57653515

UNSPSC Code:

12352200

MDL number:

MFCD00148025

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Properties

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

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

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

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M. Bernard et al.

The Journal of Organic Chemistry, 48, 3164-3164 (1983)

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 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)

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Global Trade Item Number

SKU	GTIN
93093-25G	04061833274941
93093-5G	04061833274996