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671479

Sigma-Aldrich

cataCXium® A

95%

Synonym(s):

Di(1-adamantyl)-n-butylphosphine

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About This Item

Empirical Formula (Hill Notation):
C24H39P
CAS Number:
321921-71-5
Molecular Weight:
358.54
Beilstein/REAXYS Number:
8726448
MDL number:
MFCD05861606
UNSPSC Code:
12352001
PubChem Substance ID:
329760425
NACRES:
NA.22

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Quality Level

100

assay

95%

reaction suitability

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

functional group

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-

InChI key

HTJWUNNIRKDDIV-FECFBMJZSA-N

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General description

Sold in collaboration with Solvias AG

cataCXium® A is commonly used as a catalyst in cross-coupling reactions, such as Suzuki and Sonogashira reactions. [1] [2]

Application

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,[3] Buchwald-Hartwig amination of aryl chlorides,[4] and α-arylation reactions of ketones.

Other applications:
  • palladium-catalyzed carbonylation of aryl and heteroaryl halides[5][6][7][8][9]
  • palladium-catalyzed synthesis of (hetero)aromatic nitriles[10]
  • palladium-catalyzed aminocarbonylation of aryl halides[11]

Features and Benefits

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

Legal Information

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7043
BCCL6550
BCCM3559
BCCJ8534
BCCH5006

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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)
A General Synthesis of Diarylketones by Means of a Three-Component Cross-Coupling of Aryl and Heteroaryl Bromides, Carbon Monoxide, and Boronic acids
Neumann, Helfried
Chemistry?A European Journal , 14, 3645-3652 (2008)
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Articles

cataCXium® Catalysts

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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