93093

Triphenylphosphine, polymer-bound

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

• Sinónimos: Copolymer of styrene and divinylbenzene, diphenylphosphinated, Diphenylphosphino-polystyrene, Polystyrene crosslinked with divinylbenzene, diphenylphosphinated
• Fórmula lineal: -C₆H₄P(C₆H₅)₂
• Número de CAS: 39319-11-4
• Peso molecular: 262.29
• Número MDL: MFCD00148025
• Código UNSPSC: 12352200
• ID de la sustancia en PubChem: 57653515
• NACRES: NA.22

Propiedades

• formulario: solid
• Nivel de calidad: 200
• idoneidad de la reacción: 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
• Extensión del etiquetado: ~3 mmol/g triphenylphosphine loading
• matriz: crosslinked with 2% DVB
• tamaño de partícula: 100-200 mesh
• grupo funcional: phosphine oxide
• cadena 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
• Clave InChI: RIOQSEWOXXDEQQ-UHFFFAOYSA-N

Descripción

Aplicación

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.

Otras notas

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.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Equipo de protección personal: dust mask type N95 (US), Eyeshields, Faceshields, Gloves