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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:
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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6550
BCCM3559
BCCJ8534
BCCH5006
BCCH7320

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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)
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)
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)
View All Related Papers

Articles

cataCXium® Catalysts

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

cataCXium® Catalysts

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

cataCXium® Catalysts

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

cataCXium® Catalysts

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

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