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93093

Sigma-Aldrich

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

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About This Item

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

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

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Aplicación

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]

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.[10][11]

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

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Certificados de análisis (COA)

Lot/Batch Number
BCBV1937
BCBM2609V
BCBK8391V
BCBJ8369V
BCBG3145V

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Mild and efficient esterification of alkylphosphonic acids using polymer-bound triphenylphosphine.
Purohit A K, et al.
Tetrahedron Letters, 53(29), 3795-3797 (2012)
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)
The Use of Polymer-Bound Triphenylphosphine in the Stereochemical Inversion of Secondary Alcohols.
White J M, et al.
Combinatorial Chemistry & High Throughput Screening, 3(2), 103-106 (2000)
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)
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)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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