• Chemical structure of JackiePhos (2-{bis[3,5-bis(trifluoromethyl)phenyl]phosphino}-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl), CAS 1160861-60-8, ≥98% — electron-poor dialkylbiaryl-type phosphine bearing four trifluoromethyl groups on the phosphorus aryls; ligand for palladium-catalysed cross-coupling and for cationic gold(I) catalysis. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

JackiePhos

CAS 1160861-60-8 ≥98%

JackiePhos | CAS 1160861-60-8 | ≥98%

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Technical Specifications

CAS Number 1160861-60-8
MDL Number MFCD17015286
SMILES CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)OC)OC)C(C)C
InChI InChI=1S/C39H37F12O2P/c1-19(2)22-11-29(20(3)4)33(30(12-22)21(5)6)34-31(52-7)9-10-32(53-8)35(34)54(27-15-23(36(40,41)42)13-24(16-27)37(43,44)45)28-17-25(38(46,47)48)14-26(18-28)39(49,50)51/h9-21H,1-8H3
InChIKey KYTUFIMHJNRPLC-UHFFFAOYSA-N
PubChem CID 44597232
Molecular Formula C₃₉H₃₇F₁₂O₂P
Molecular Weight 796.7 g/mol
Melting Point 186–190 °C
Solubility Insoluble in water, soluble in common organic solvents
Purity ≥98%
Physical Form White to off-white solid
HS Code 2931.49
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store in a tightly sealed container under inert gas (N₂ or Ar)

Product Description & Scientific Applications

JackiePhos is the electron-poor member of the biaryl phosphine family: four trifluoromethyl groups on the phosphorus aryls strip electron density from phosphorus, reversing the design logic of every electron-rich biaryl ligand.

It was first reported for the palladium-catalysed amidation of aryl halides, and the electron-poor phosphorus is what makes it useful where the standard ligands stall — reductive elimination from an electron-poor metal centre is faster, not slower.

Applications and Reactions

  • Couplings where electron-rich ligands fail: in one coupling, electron-rich dialkylbiaryl phosphines gave only traces of the desired product while this ligand carried the reaction to 58%. It has also been applied to Stille cross-coupling of aryl iodides with ester-substituted cyclopropylstannanes.
  • C-Glycosylation: screened against more than fifty phosphines, it was the one that most effectively minimised the competing elimination to the glycal, delivering the C-glycoside in 94% yield with exclusive selectivity. The effect was attributed to suppressing the degradative elimination pathway and promoting reductive elimination at the same time.
  • Gold(I) catalysis: an electron-poor ligand favours electronic activation of the alkyne where that activation is rate-determining. On that basis it converted two substrates that had been unreactive under the previous conditions, both in good yield.
  • Documented limits: in one amination screen an adamantyl-substituted ligand outperformed it along with three other phosphines. In a re-examined alkene diamination its absence did not alter the outcome at all — the acetylacetonate proved to be the operative ligand, and the phosphine was not binding the palladium.

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.

Shipping Destinations

  • EU & UK: Priority delivery, 2–5 business days.
  • United States (DDP): 3–7 business days, duties and taxes prepaid.
  • EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
  • 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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