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Merck
CN

93093

Triphenylphosphine, polymer-bound

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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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

~3 mmol/g triphenylphosphine loading

matrix

crosslinked with 2% DVB

particle size

100-200 mesh

functional group

phosphine oxide

Quality Level

200

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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.

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
BCBV1937
BCBM2609V
BCBK8391V
BCBJ8369V
BCBG3145V

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M. Bernard et al.
The Journal of Organic Chemistry, 48, 3164-3164 (1983)
Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation.
Ley S V, et al.
Journal of the Chemical Society. Perkin Transactions 1, 23, 3815-4195 (2000)
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)
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)
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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