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Sigma-Aldrich

cataCXium® A

95%

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Synonym(s):
Di(1-adamantyl)-n-butylphosphine
Empirical Formula (Hill Notation):
C24H39P
CAS Number:
321921-71-5
Molecular Weight:
358.54
Beilstein:
8726448
MDL number:
MFCD05861606
UNSPSC Code:
12352001
PubChem Substance ID:
329760425
NACRES:
NA.22

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

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
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)
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.

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