• Chemical structure of cataCXium A (di(1-adamantyl)-n-butylphosphine), CAS 321921-71-5, ≥97% — bulky, strongly electron-donating monodentate trialkylphosphine with two adamantyl cages and an n-butyl chain on phosphorus; ligand for palladium-catalysed Suzuki–Miyaura, Heck, Sonogashira and Buchwald–Hartwig coupling of aryl chlorides, α-arylation of ketones and carbonylation. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

cataCXium A

CAS 321921-71-5 ≥97%

cataCXium A | CAS 321921-71-5 | ≥97%

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Technical Specifications

CAS Number 321921-71-5
EC / EINECS Number 691-708-4
MDL Number MFCD05861606
SMILES CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
InChI 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
InChIKey HTJWUNNIRKDDIV-UHFFFAOYSA-N
PubChem CID 11371790
Molecular Formula C₂₄H₃₉P
Molecular Weight 358.5 g/mol
Melting Point 100–110 °C
Solubility Insoluble in water, soluble in common organic solvents
Purity ≥97%
Physical Form White to yellow solid
HS Code 2931.49
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store under inert gas (N₂ or Ar) in a tightly sealed container

Product Description & Scientific Applications

cataCXium A (di(1-adamantyl)-n-butylphosphine) is a bulky, electron-rich trialkylphosphine: the two adamantyl cages supply both the steric bulk and the electron density at phosphorus that let palladium turn over unactivated aryl chlorides.

The free ligand oxidises slowly in air and is handled and stored under inert gas — nothing shields the lone pair the way the second ring does in a biaryl phosphine. The hydriodide salt and the palladium precatalysts derived from it exist for that reason.

Applications and Reactions

  • Cross-coupling of non-activated and deactivated aryl chlorides: the founding application and still the defining one. Palladium with this ligand couples aryl chloride substrates across the Suzuki–Miyaura, Heck and Sonogashira manifolds, in Buchwald–Hartwig amination, and in α-arylation of ketones.
  • Formylation and carbonylation: palladium acetate with this ligand and TMEDA is the benchmark system for formylation of aryl and heteroaryl bromides with synthesis gas, run on multi-tonne scale for pharmaceutical aldehyde intermediates. The same ligand carries the wider carbonylation family — aminocarbonylation of aryl and heteroaryl halides, alkoxycarbonylation of aryl bromides with phenols to aryl esters at 1–2 bar CO, carbonylative Suzuki coupling to diaryl ketones, and synthesis of aromatic nitriles.
  • Alkyl coupling partners: potassium alkyltrifluoroborates couple with aryl and heteroaryl chlorides under palladium with this ligand, giving access to secondary alkyl–aryl bonds.

Further Reading

Practical guidance on choosing a phosphine ligand for palladium- and nickel-catalysed cross-coupling in NorrChemica's Lab Journal: Phosphine Ligands for Cross-Coupling.

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  • Worldwide: 7–14 business days, selected locations.

Safety Information

Hazard Class Not regulated for transport
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)
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