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671479

Sigma-Aldrich

Di(1-adamantyl)-n-butylphosphine

95%

Sinónimos:

cataCXium® A

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About This Item

Fórmula empírica (notación de Hill):
C24H39P
Número de CAS:
321921-71-5
Peso molecular:
358.54
Beilstein/REAXYS Number:
8726448
MDL number:
MFCD05861606
UNSPSC Code:
12352001
PubChem Substance ID:
329760425
NACRES:
NA.22

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

Categorías relacionadas

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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)
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)
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)
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Artículos

cataCXium® Catalysts

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

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