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Merck
CN

671479

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
UNSPSC Code:
12352001
NACRES:
NA.22
PubChem Substance ID:
329760425
MDL number:
MFCD05861606
Beilstein/REAXYS Number:
8726448

Key Documents

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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

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

Quality Level

100

Related Categories

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.

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, Buchwald-Hartwig amination of aryl chlorides, and α-arylation reactions of ketones.

Other applications:
  • palladium-catalyzed carbonylation of aryl and heteroaryl halides
  • palladium-catalyzed synthesis of (hetero)aromatic nitriles
  • palladium-catalyzed aminocarbonylation of aryl halides

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

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
BCCN4016
0000456267
0000456267
BCCM7043
BCCL6550

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Efficient carbonylation of aryl and heteroaryl bromides using a palladium/diadamantylbutylphosphine catalyst
Neumann H, et al.
Advanced Synthesis & Catalysis, 348(10-11), 1255-1261 (2006)
Palladium-catalyzed carbonylation reactions of aryl halides and related compounds
Brennfuhrer A, et al.
Angewandte Chemie (International Edition in English), 48(23), 4114-4133 (2009)
Selective Palladium-Catalyzed Aminocarbonylation of Aryl Halides with CO and Ammonia
Wu, Xiao-Feng and Neumann, Helfried and Beller, Matthias
Chemistry?A European Journal , 16(32), 9750-9753 (2010)
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 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)
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Articles

cataCXium® Catalysts

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

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