• Chemical structure of DPEphos (bis[2-(diphenylphosphino)phenyl] ether), CAS 166330-10-5, ≥97% — flexible wide-bite-angle bidentate diphosphine with a diaryl ether backbone and a natural bite angle near 102°; ligand for palladium-catalysed Buchwald–Hartwig amination and carbonylation, ruthenium hydrogen-borrowing amine synthesis and Cu(I) emitters. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

DPEphos

CAS 166330-10-5 ≥97%

DPEphos | CAS 166330-10-5 | ≥97%

Pack sizes & prices

Pack size Excl. VAT
5.0 g €71,08€14,22/g€89,20 incl. VAT
10 g €102,95€10,30/g€129,20 incl. VAT
25 g €142,79€5,71/g€179,20 incl. VAT
100 g €198,57€1,99/g€249,20 incl. VAT
500 g €737,05€1,47/g€925,00 incl. VAT

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Technical Specifications

CAS Number 166330-10-5
EC / EINECS Number 678-206-0
MDL Number MFCD00233863
SMILES C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6
InChI InChI=1S/C36H28OP2/c1-5-17-29(18-6-1)38(30-19-7-2-8-20-30)35-27-15-13-25-33(35)37-34-26-14-16-28-36(34)39(31-21-9-3-10-22-31)32-23-11-4-12-24-32/h1-28H
InChIKey RYXZOQOZERSHHQ-UHFFFAOYSA-N
PubChem CID 4285986
Molecular Formula C₃₆H₂₈OP₂
Molecular Weight 538.6 g/mol
Melting Point 184–187 °C
Solubility Insoluble in water, soluble in common organic solvents
Purity ≥97%
Physical Form White to off-white crystalline powder
HS Code 2931.90
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Keep container tightly closed. Store in a cool and shaded area

Product Description & Scientific Applications

DPEphos (bis[2-(diphenylphosphino)phenyl] ether) is a flexible large-bite-angle diphosphine: two phosphorus donors bridged by a diaryl ether whose oxygen can itself coordinate as a third site.

Backbone flexibility and the wide bite angle are the primary features determining the properties of this ligand. The flexibility allows cis, trans and hemilabile P,O,P coordination modes to be adopted, and the ligand resists the phosphorus–carbon degradation reactions reported for tertiary phosphine metal complexes. Xantphos is susceptible to P–C bond activation at room temperature; cleavage of DPEphos is restricted to a single reported example, at high temperature and at a carbon–oxygen bond.

Applications and Reactions

  • Bite angle and cross-coupling selectivity: rate and selectivity both rise with increasing bite angle and reach a maximum at DPEphos, 102.7°. Larger bite angles than that give decreased selectivity and activity, so a wider ligand is no guide to a faster reaction.
  • Rhodium-catalysed hydroformylation: the wide bite angle is the reason the ligand is used here, alongside Xantphos.
  • Copper(I) emitters: an organic light-emitting diode built on a copper complex of this ligand reached 15.0% external quantum efficiency, comparable to devices based on iridium emitters.
  • Visible-light photocatalysis: the copper neocuproine complex drove photocyclisation of a stilbene precursor to a helicene.
  • Bite-angle mismatch: in one cycloaddition, complexes of this ligand and of three other wide-bite-angle diphosphines failed to affect the reaction at all.

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.

Shipping Destinations

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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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