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93093

Triphenylphosphine, polymer-bound

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

Synonim(y):

Copolymer of styrene and divinylbenzene, diphenylphosphinated, Diphenylphosphino-polystyrene, Polystyrene crosslinked with divinylbenzene, diphenylphosphinated

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Informacje o tej pozycji

Wzór liniowy:
-C6H4P(C6H5)2
Numer CAS:
Masa cząsteczkowa:
262.29
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
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form

solid

Quality Level

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 mmol/g triphenylphosphine loading

matrix

crosslinked with 2% DVB

particle size

100-200 mesh

functional group

phosphine oxide

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

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.

Other Notes

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.
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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów



M. Bernard et al.
The Journal of Organic Chemistry, 48, 3164-3164 (1983)
Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation.
Ley S V, et al.
Journal of the Chemical Society. Perkin Transactions 1, 23, 3815-4195 (2000)
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)



Numer pozycji handlu globalnego

SKUNUMER GTIN
93093-25G04061833274941
93093-5G04061833274996

Questions

1–2 of 2 Questions  
  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/418/501/product-dating-information-06-25-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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