• Chemical structure of AdBippyPhos (5-[di(1-adamantyl)phosphino]-1',3',5'-triphenyl-1'H-[1,4']bipyrazole), CAS 1239478-87-5, ≥97% — bulky electron-rich bipyrazole-backboned phosphine carrying two adamantyl cages on phosphorus; ligand for palladium-catalysed Buchwald-Hartwig amination and difficult C–N couplings. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

Ad-BippyPhos

CAS 1239478-87-5 ≥97%

Ad-BippyPhos | CAS 1239478-87-5 | ≥97%

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Technical Specifications

CAS Number 1239478-87-5
MDL Number MFCD22200502
SMILES C1C2CC3CC1CC(C2)(C3)P(C4=CC=NN4C5=C(N(N=C5C6=CC=CC=C6)C7=CC=CC=C7)C8=CC=CC=C8)C91CC2CC(C9)CC(C2)C1
InChI InChI=1S/C44H47N4P/c1-4-10-36(11-5-1)40-42(41(37-12-6-2-7-13-37)47(46-40)38-14-8-3-9-15-38)48-39(16-17-45-48)49(43-24-30-18-31(25-43)20-32(19-30)26-43)44-27-33-21-34(28-44)23-35(22-33)29-44/h1-17,30-35H,18-29H2
InChIKey IHFBOUNFWVRWAQ-UHFFFAOYSA-N
PubChem CID 46939809
Molecular Formula C₄₄H₄₇N₄P
Molecular Weight 662.8 g/mol
Melting Point 295–300 °C
Solubility Insoluble in water, soluble in common organic solvents including dichloromethane and tetrahydrofuran
Purity ≥97%
Physical Form White to yellow crystalline solid
HS Code 2933.19
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store refrigerated (2–8 °C) in a tightly sealed container under inert gas (N₂ or Ar)

Product Description & Scientific Applications

AdBippyPhos is BippyPhos with adamantyl cages in place of the tert-butyl groups on phosphorus, on the same bipyrazole backbone.

It is supplied under inert atmosphere and stored refrigerated. Its value in carbon–oxygen coupling rests on favouring carbon–oxygen reductive elimination over the competing hydride elimination that consumes the alkoxide partner.

Applications and Reactions

  • N-Arylation of sulfonamides: a practical and general method arylates weakly nucleophilic sulfonamides on palladium with this ligand, coupling both aryl bromides and chlorides at 3 mol% of a crotyl palladium chloride dimer with 12 mol% ligand. Two other phosphine families were screened alongside it and this ligand gave the highest conversion.
  • Aryl alkyl ethers: it is named among the most effective ancillary ligands reported for challenging palladium carbon–oxygen cross-couplings, and its protocols are simpler than a rival ligand that requires a carefully preformed catalyst together with molecular sieves or trialkylamine additives. In pharmaceutical development work it was identified as invaluable for coupling a secondary alcohol with an aryl halide.
  • Fluoroalkylamines: in palladium-catalysed carbon–nitrogen couplings of fluoroalkylamines it outperformed four other ligands examined, among them tBuBrettPhos and JackiePhos.
  • Indole arylation: one of five ligands effective in the arylation of indole, giving high yields of the phenylindole.
  • Where it is outperformed: its reported carbon–oxygen scope covers only a limited number of primary aliphatic alcohols, and RockPhos routinely beat it for primary and secondary alcohols with aryl halides at room temperature, though heating to 90 °C made it competitive again. In the selective monoarylation of ammonia it was not among the effective ligands, where Josiphos, MorDalPhos and BippyPhos were.

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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Safety Information

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