• Chemical structure of DavePhos (2′-(dicyclohexylphosphino)-N,N-dimethyl-[1,1′-biphenyl]-2-amine), CAS 213697-53-1, ≥98% — electron-rich dialkylbiaryl phosphine, among the earliest of the Buchwald ligands, carrying a dimethylamino group ortho on the second ring for palladium-catalysed Buchwald–Hartwig amination and Suzuki–Miyaura coupling of aryl halides. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

DavePhos

CAS 213697-53-1 ≥98%

DavePhos | CAS 213697-53-1 | ≥98%

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Technical Specifications

CAS Number 213697-53-1
EC / EINECS Number 606-749-5
MDL Number MFCD02183572
SMILES CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
InChI InChI=1S/C26H36NP/c1-27(2)25-19-11-9-17-23(25)24-18-10-12-20-26(24)28(21-13-5-3-6-14-21)22-15-7-4-8-16-22/h9-12,17-22H,3-8,13-16H2,1-2H3
InChIKey ZEMZPXWZVTUONV-UHFFFAOYSA-N
PubChem CID 2734217
Molecular Formula C₂₆H₃₆NP
Molecular Weight 393.5 g/mol
Melting Point 121-124 °C (lit.)
Solubility Soluble in THF, 1,4-dioxane, toluene, dichloromethane and ethyl acetate; practically insoluble in water. Air-sensitive in solution — prepare in degassed solvents under inert atmosphere.
Purity ≥98%
Physical Form Solid
HS Code 2931.90
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store at room temperature in a tightly sealed container under inert atmosphere, protected from moisture

Product Description & Scientific Applications

DavePhos is a dicyclohexylphosphine carrying a dimethylamino group ortho on the second ring, and among the earliest of the Buchwald series. It was made and explored for palladium-catalysed C–N coupling, giving a highly active catalyst for amination of aryl bromides and chlorides. That activity allowed amination of a number of aryl bromides — and one activated aryl chloride — at room temperature.

Process scale. There is a documented example of this ligand at manufacturing scale: 1-chloro-4-trifluoromethylbenzene coupled to a chiral amine with palladium acetate at sub-percent loading, delivering the key aniline intermediate on multikilogram scales. Catalytic phenylboronic acid was needed to preactivate the catalyst, and since the aniline was an oil the amination was telescoped into the subsequent hydrolysis, giving the crystalline amide in 74 to 79% overall yield.

Benzylic C–H functionalisation. 2-Alkyl N-iminopyridinium ylides undergo benzylic C–H functionalisation under relatively mild conditions, with aryl chlorides carrying either electron-withdrawing or electron-donating groups, in 43 to 94% yield. With excess aryl chloride the arylation goes twice.

Desulfinative coupling. Aryl sulfinates couple with 3-haloquinolines in good to excellent yields, at a 2:1 ligand-to-palladium ratio with a dibenzylideneacetone source. The conditions were optimised for the iodoquinolines: only two aryl sulfinates were successfully employed, and with bromides competitive nucleophilic aromatic substitution was observed.

Beyond amination. Substituting it into a cascade C–H trifluoroethylation of aryl iodides raised the yield to 50%. Switching the palladium source with this ligand suppressed the competing product completely, giving one product exclusively in high yield. It is also the ligand of a mechanochemical Suzuki system built on palladium acetate with cyclooctadiene as stabilising additive and water.

Off-cycle pathway. The arylpalladium complex has a vacant coordination site, which another such complex may trap — forming a dimer observed experimentally with this ligand.

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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