93093

Sigma-Aldrich

Triphenylphosphine, polymer-bound

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

Synonym(s):
Polystyrene crosslinked with divinylbenzene, diphenylphosphinated, Copolymer of styrene and divinylbenzene, diphenylphosphinated, Diphenylphosphino-polystyrene
Linear Formula:
-C6H4P(C6H5)2
CAS Number:
Molecular Weight:
262.29
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

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

Quality Level

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

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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.

Packaging

5, 25 g in glass bottle

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis
Certificate of Origin
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 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)
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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