93093

Triphenylphosphine, polymer-bound

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

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

Propriedades

• Formulário: solid
• Nível de qualidade: 200
• adequação da reação: 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
• Extensão da rotulagem: ~3 mmol/g triphenylphosphine loading
• Matriz: crosslinked with 2% DVB
• tamanho de partícula: 100-200 mesh
• grupo funcional: phosphine oxide
• cadeia de caracteres 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
• chave InChI: RIOQSEWOXXDEQQ-UHFFFAOYSA-N

Descrição

Aplicação

Polymer-bound triphenylphosphine is a solid-supported reagent[1] that can be used as a better alternative to triphenylphosphine in the Mitsunobu reaction.[2][3]
It can also be used:

• For the esterification of alkylphosphonic acids using primary alcohols in the presence of iodine and imidazole.[4]
• 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.[5]
• To isomerize (Z)-nitro olefins to the (E)-isomers.[6]
• To prepare polymer-bound ylides which are useful in Wittig reactions.[7]
• To convert alcohols or carboxylic acids to the corresponding chlorides.[8]
• In combination with carbon tetrachloride for the coupling N-alkoxycarbonyl α-amino acids and primary amines to form the corresponding amides.[9]

Outras 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.[10][11]

Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Equipamento de proteção individual: dust mask type N95 (US), Eyeshields, Faceshields, Gloves