• Chemical structure of Cy-BippyPhos (5-(dicyclohexylphosphino)-1′,3′,5′-triphenyl-1′H-[1,4′]bipyrazole), CAS 1021176-69-1, ≥98% — electron-rich bipyrazole-backboned phosphine, the dicyclohexyl analogue of BippyPhos; ligand for palladium-catalysed Buchwald–Hartwig amination of (hetero)aryl chlorides and bromides, particularly secondary amines, where the bulkier family members suffer competitive hydroxylation. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

Cy-BippyPhos

CAS 1021176-69-1 ≥98%

Cy-BippyPhos | CAS 1021176-69-1 | ≥98%

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Technical Specifications

CAS Number 1021176-69-1
MDL Number MFCD11616511
SMILES C1CCC(CC1)P(C2CCCCC2)C3=CC=NN3C4=C(N(N=C4C5=CC=CC=C5)C6=CC=CC=C6)C7=CC=CC=C7
InChI InChI=1S/C36H39N4P/c1-6-16-28(17-7-1)34-36(35(29-18-8-2-9-19-29)39(38-34)30-20-10-3-11-21-30)40-33(26-27-37-40)41(31-22-12-4-13-23-31)32-24-14-5-15-25-32/h1-3,6-11,16-21,26-27,31-32H,4-5,12-15,22-25H2
InChIKey ZMENEJKATASVIH-UHFFFAOYSA-N
PubChem CID 53430914
Molecular Formula C₃₆H₃₉N₄P
Molecular Weight 558.7 g/mol
Melting Point 177–180 °C
Solubility Soluble in THF, 1,4-dioxane, toluene, dichloromethane and ethyl acetate. In solution the ligand should be manipulated in degassed solvents to avoid oxidation
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

Cy-BippyPhos is the dicyclohexylphosphino member of the triphenylbipyrazole phosphine family; BippyPhos and Ad-BippyPhos are the di-tert-butyl and diadamantyl analogues. It is the least sterically demanding of the three.

Suzuki–Miyaura coupling of hindered substrates. With potassium carbonate as base, the coupling of 2,6-dimethylchlorobenzene with phenylboronic acid gives 98% conversion against 35% for BippyPhos; for 1-naphthylboronic acid with 1-bromo-2-methoxynaphthalene the figures are 95% and 5%. It exceeds BippyPhos in every reported case with multiple ortho substituents. Substitution of potassium hydroxide for potassium carbonate increases reactivity further, and under those conditions a tetra-ortho-substituted biaryl is obtained in 91% conversion. Reported conditions: Pd(OAc)2, 2:1 ligand-to-palladium, tert-amyl alcohol at reflux (100–103 °C), 3 h.

Amination of secondary amines and anilines. N-Benzylmethylamine couples with 2-bromo-6-methoxypyridine at 99% conversion with no detected side product; BippyPhos gives 92% with 8% hydroxylated adduct.

Limitations. Primary amines undergo competitive bis-arylation: phenethylamine gives 71% of the desired product with 24% bis-arylated adduct, against 96% and 3% for BippyPhos. Electron-rich aryl halides favour β-hydride elimination; with 2-chloroanisole conversion is 45% with 38% anisole. The ligand is unsuitable for C–O coupling: with methanol only the reduction product is obtained.

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)

Documentation

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