• Chemical structure of BippyPhos (5-(di-tert-butylphosphino)-1′,3′,5′-triphenyl-1′H-[1,4′]bipyrazole), CAS 894086-00-1, ≥98% — bulky electron-rich bipyrazole phosphine ligand for palladium-catalysed amination of aryl halides including aryl chlorides, typically paired with Pd₂(dba)₃, and non-proprietary. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

BippyPhos

CAS 894086-00-1 ≥98%

BippyPhos | CAS 894086-00-1 | ≥98%

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Technical Specifications

CAS Number 894086-00-1
EC / EINECS Number 814-047-7
MDL Number MFCD09038440
SMILES CC(C)(C)P(C1=CC=NN1C2=C(N(N=C2C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5)C(C)(C)C
InChI InChI=1S/C32H35N4P/c1-31(2,3)37(32(4,5)6)27-22-23-33-36(27)30-28(24-16-10-7-11-17-24)34-35(26-20-14-9-15-21-26)29(30)25-18-12-8-13-19-25/h7-23H,1-6H3
InChIKey PTXJGGGNGMPMBG-UHFFFAOYSA-N
PubChem CID 11547931
Molecular Formula C₃₂H₃₅N₄P
Molecular Weight 506.62 g/mol
Melting Point 169–173 °C
Solubility Soluble in THF, 1,4-dioxane, toluene, dichloromethane and ethyl acetate. Air-sensitive in solution — prepare in degassed solvents under inert atmosphere.
Purity ≥98%
Physical Form White crystalline solid
HS Code 2933.19
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store in a cool, dry place in a tightly sealed container, protected from air and moisture. Relatively air-stable

Product Description & Scientific Applications

BippyPhos is a bulky, electron-rich bipyrazole phosphine, built on two linked pyrazole rings rather than the biphenyl of the Buchwald ligands. It is air-stable, soluble in common organic solvents, and non-proprietary.

C–N coupling. This is the ligand's primary application. In a screen across several ligands, only BippyPhos gave appreciable yields of every desired C–N cross-coupling product. Its catalyst systems couple primary and secondary amines, substituted hydroxylamines, ureas and imidazoles. It is among the ligands proven effective in palladium-catalysed monoarylation of ammonia, where over-arylation ordinarily competes.

Hydroxylation to phenols. With a palladium dibenzylideneacetone source it forms a robust system for hydroxylation of aryl and heteroaryl halides, under mild conditions and across a broad substrate scope. Haloarylacetylenes hydroxylate and close to the benzofuran in the same operation. On that transformation it outperformed two hindered biarylphosphine ligands.

Binding mode. The first crystallographically characterised palladium(II) complex showed a bidentate motif resembling the biarylphosphine class, coordinating through phosphorus in a κ²-P,C fashion.

Limits. It was not designed for Suzuki–Miyaura coupling, though it has been shown to work there: the parent ligand suffices for unhindered partners, while substrates carrying multiple ortho substituents require less hindered analogues for high yields. For coupling of primary and secondary alcohols, RockPhos has generally been considered the optimal ligand. In one comparison BippyPhos showed high reactivity but lower selectivity.

Further reading: For phosphine-ligand selection, palladium sources and precatalysts, and Suzuki–Miyaura and Buchwald–Hartwig reagent choice, see NorrChemica's Lab Journal guide: 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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