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671479

Sigma-Aldrich

Di(1-adamantyl)-n-butylphosphine

95%

Sinonimo/i:

cataCXium® A

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About This Item

Formula empirica (notazione di Hill):
C24H39P
Numero CAS:
321921-71-5
Peso molecolare:
358.54
Beilstein:
8726448
Numero MDL:
MFCD05861606
Codice UNSPSC:
12352001
ID PubChem:
329760425
NACRES:
NA.22

Saggio

95%

Impiego in reazioni chimiche

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

Gruppo funzionale

phosphine

Stringa SMILE

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-
HTJWUNNIRKDDIV-FECFBMJZSA-N

Categorie correlate

Descrizione generale

Sold in collaboration with Solvias AG

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

Applicazioni

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

Caratteristiche e vantaggi

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

Note legali

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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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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Articoli

cataCXium® Catalysts

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

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