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14664

Sigma-Aldrich

Triphenylphosphine, polymer-bound

100-200 mesh, extent of labeling: ~3.2 mmol/g 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
MDL number:
MFCD00148025
UNSPSC Code:
12352128
PubChem Substance ID:
57647187
NACRES:
NA.22

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

~3.2 mmol/g loading

matrix

crosslinked with 2% DVB

particle size

100-200 mesh

functional group

phosphine

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

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Application

Polymer-bound triphenylphosphine (PPh3) is a reusable organocatalyst for the Mukaiyama aldol and Mannich reaction. It can also be used as a traceless reagent for Mitsunobu reaction in combinatorial chemistry to synthesize aryl ethers from phenols and alcohols.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Polymer-supported PPh 3 as a reusable organocatalyst for the Mukaiyama aldol and Mannich reaction.
Matsukawa S, et al.
Royal Society of Chemistry Advances, 4(53), 27780-27786 (2014)
Polymer-bound triphenylphosphine as traceless reagent for Mitsunobu reactions in combinatorial chemistry: Synthesis of aryl ethers from phenols and alcohols.
Tunoori A R, et al.
Tetrahedron Letters, 39(48), 8751-8754 (1998)
Crispin Lichtenberg et al.
Dalton transactions (Cambridge, England : 2003), 44(46), 20056-20066 (2015-11-04)
A diolefin ether, trop2O (2), and a diolefin thioether, trop2S (3), have been investigated as ligand analogues of the well-established diolefin amine, trop2NH (1). Compounds 2 and 3 form different conformers in solution and in the solid state. Whereas 2
Uday Narayan Maiti et al.
ACS applied materials & interfaces, 7(46), 25898-25905 (2015-11-03)
A scalable and controllable nanoscale perforation method for graphene is developed on the basis of the two-step thermal activation of a graphene aerogel. Different resistance to the thermal oxidation between graphitic and defective domains in the weakly reduced graphene oxide
Jasmin Awad et al.
Plant physiology, 167(4), 1592-1603 (2015-02-11)
Different peroxidases, including 2-cysteine (2-Cys) peroxiredoxins (PRXs) and thylakoid ascorbate peroxidase (tAPX), have been proposed to be involved in the water-water cycle (WWC) and hydrogen peroxide (H2O2)-mediated signaling in plastids. We generated an Arabidopsis (Arabidopsis thaliana) double-mutant line deficient in
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