• Chemical structure of AdBrettPhos (2-[di(1-adamantyl)phosphino]-3,6-dimethoxy-2',4',6'-triisopropylbiphenyl), CAS 1160861-59-5, ≥95% — bulky electron-rich dialkylbiaryl phosphine carrying two adamantyl cages on phosphorus; ligand for palladium-catalysed monoarylation of ammonia, couplings of five-membered heteroarenes, fluorination of aryl triflates and C–O coupling of primary alcohols. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

AdBrettPhos

CAS 1160861-59-5 ≥95%

AdBrettPhos | CAS 1160861-59-5 | ≥95%

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Technical Specifications

CAS Number 1160861-59-5
MDL Number MFCD23379935
SMILES CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C34CC5CC(C3)CC(C5)C4)C67CC8CC(C6)CC(C8)C7)OC)OC)C(C)C
InChI InChI=1S/C43H61O2P/c1-25(2)34-17-35(26(3)4)39(36(18-34)27(5)6)40-37(44-7)9-10-38(45-8)41(40)46(42-19-28-11-29(20-42)13-30(12-28)21-42)43-22-31-14-32(23-43)16-33(15-31)24-43/h9-10,17-18,25-33H,11-16,19-24H2,1-8H3
InChIKey NMGHOZQCYNKWBG-UHFFFAOYSA-N
PubChem CID 60144828
Molecular Formula C₄₃H₆₁O₂P
Molecular Weight 640.9 g/mol
Melting Point 231–235 °C
Solubility Insoluble in water, soluble in common organic solvents
Purity ≥95%
Physical Form White to off-white solid
HS Code 2931.49
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), protected from light

Product Description & Scientific Applications

AdBrettPhos is a bulky biaryl phosphine carrying two adamantyl cages on phosphorus, where BrettPhos carries tert-butyl groups.

It is normally deployed as a preformed palladium precatalyst rather than mixed in situ, and which precatalyst matters: the halide-free cyclooctadiene dimer avoids the competitive chlorination seen with a cinnamyl palladium chloride source.

Applications and Reactions

  • Amidation of five-membered heterocycles: the founding application. Earlier ligands were deficient on five-membered heterocyclic halides bearing several heteroatoms, with success largely confined to aniline nucleophiles. This ligand gave the first palladium-catalysed amidation of multi-heteroatom five-membered heterocyclic bromides.
  • Primary anilines without double arylation: introducing a single amino group is difficult because double arylation competes. With a methylnaphthyl palladium bromide precatalyst it converts non-activated aryl chlorides to primary anilines in 30 minutes at 80 °C, including drug-like substrates.
  • Fluorination of aryl and heteroaryl triflates: a stable palladium cyclooctadiene complex of this ligand catalyses fluorination of functionalised aryl and heteroaryl triflates with caesium fluoride, and catalysts built on it brought aryl bromides within reach of the reaction.
  • Regioselective triazole arylation: with an allyl palladium precatalyst it gives selective arylation at the second nitrogen of monosubstituted triazoles.
  • C–O coupling: reported for the palladium-catalysed cross-coupling of primary alcohols with aryl halides.
  • Documented limits: in one solvent screen another ligand outperformed it and three further phosphines. With excess ammonium triflate and base, the naphthyl group of the palladium precatalyst was itself aminated as the major product.

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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