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Merck

671479

Sigma-Aldrich

Di-(1-adamantyl)-n-butylphosphin

95%

Synonym(e):

cataCXium® A

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€ 99,50
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50 G
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100 G
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250 G
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About This Item

Empirische Formel (Hill-System):
C24H39P
CAS-Nummer:
Molekulargewicht:
358.54
Beilstein:
8726448
MDL-Nummer:
UNSPSC-Code:
12352001
PubChem Substanz-ID:
NACRES:
NA.22

€ 99,50


Voraussichtliches Versanddatum13. April 2025


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Qualitätsniveau

Assay

95%

Eignung der Reaktion

reagent type: ligand
reaction type: Arylations

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: C-C Bond Formation

reagent type: ligand
reaction type: Cross Couplings

reagent type: ligand
reaction type: Heck Reaction

reagent type: ligand
reaction type: Sonogashira Coupling

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Funktionelle Gruppe

phosphine

SMILES String

CCCCP([C@]12C[C@H]3C[C@H](C[C@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5

InChI

1S/C24H39P/c1-2-3-4-25(23-11-17-5-18(12-23)7-19(6-17)13-23)24-14-20-8-21(15-24)10-22(9-20)16-24/h17-22H,2-16H2,1H3/t17-,18+,19-,20-,21+,22-,23-,24-

InChIKey

HTJWUNNIRKDDIV-FECFBMJZSA-N

Allgemeine Beschreibung

Verkauf in Zusammenarbeit mit Solvias AG

Anwendung

cataCXium® A or di-adamantylalkylphosphine is a bulky and electron-rich phosphine ligand that is highly effective for palladium catalyzed cross-coupling reactions such as Heck and Suzuki coupling,[1] Buchwald-Hartwig amination of aryl chlorides,[2] and α-arylation reactions of ketones.

Other applications:
  • palladium-catalyzed carbonylation of aryl and heteroaryl halides[3][4][5][6][7]
  • palladium-catalyzed synthesis of (hetero)aromatic nitriles[8]
  • palladium-catalyzed aminocarbonylation of aryl halides[9]

Leistungsmerkmale und Vorteile

  • Mild reaction condition
  • Low catalyst loading
  • High yield and turn over number

Rechtliche Hinweise

US7148176
cataCXium is a registered trademark of Umicore AG & Co. KG

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Besitzen Sie dieses Produkt bereits?

In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

A general and efficient method for the formylation of aryl and heteroaryl bromides
Klaus S, et al.
Angewandte Chemie (International Edition in English), 45(1), 154-158 (2006)
Efficient carbonylation of aryl and heteroaryl bromides using a palladium/diadamantylbutylphosphine catalyst
Neumann H, et al.
advanced synthesis and catalysis, 348(10-11), 1255-1261 (2006)
An Efficient and Practical Sequential One-Pot Synthesis of Suprofen, Ketoprofen and Other 2-Arylpropionic Acids
Neumann H, et al.
advanced synthesis and catalysis, 350(14-15), 2437-2442 (2008)
Convenient Carbonylation of Aryl Bromides with Phenols to Form Aryl Esters by Applying a Palladium/Di-1-adamantyl-n-butylphosphine Catalyst
Wu, Xiao-Feng and Neumann, Helfried and Beller, Matthias
ChemCatChem, 2(5), 509-513 (2010)
An Efficient and Practical Sequential One-Pot Synthesis of Suprofen, Ketoprofen and Other 2-Arylpropionic Acids
Neumann H, et al.
Advanced Synthesis & Catalysis, 350(14-15), 2437-2442 (2008)

Artikel

cataCXium® ligands facilitate cross-coupling reactions, essential in polymer science, fine chemicals, and pharmaceutical industries.

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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