93093

Triphenylphosphine, polymer-bound

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

• Synonyme(s) : Copolymer of styrene and divinylbenzene, diphenylphosphinated, Diphenylphosphino-polystyrene, Polystyrene crosslinked with divinylbenzene, diphenylphosphinated
• Formule linéaire : -C₆H₄P(C₆H₅)₂
• Numéro CAS: 39319-11-4
• Poids moléculaire : 262.29
• Numéro MDL: MFCD00148025
• Code UNSPSC : 12352200
• ID de substance PubChem : 57653515
• Nomenclature NACRES : NA.22

Propriétés

• Forme: solid
• Niveau de qualité: 200
• Capacité de réaction: 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
• Pertinence de la réaction: reagent type: ligand
• Ampleur du marquage: ~3 mmol/g triphenylphosphine loading
• Matrice: crosslinked with 2% DVB
• Taille des particules: 100-200 mesh
• Groupe fonctionnel: phosphine oxide
• Chaîne SMILES: 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
• Clé InChI: 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.

Autres remarques

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Faceshields, Gloves