o-Phenanthroline

Technical Specifications

Product Description & Scientific Applications

1,10-Phenanthroline, also sold as o-phenanthroline, is a rigid, planar bidentate N-donor ligand whose optimally oriented nitrogen atoms coordinate strongly to most metals, especially transition metals, lanthanides and actinides.

Its extended conjugation over three fused rings makes it an electron-deficient, strong-acceptor ligand that stabilises soft metal cations. Unlike bipyridine, its extra fused ring blocks ligand rotation, giving more rigid catalyst complexes.

Applications and Reactions

• Copper-catalysed Ullmann amination: it enables amination of aryl halides with amines at 110 °C and 10 mol% copper, below the classical stoichiometric-copper method.
• Copper C–S coupling: with Cu₂O it supports coupling of aryl halides with thiols in 75–99% yield.
• CuAAC click chemistry: added to copper(I) catalysts it accelerates azide–alkyne cycloaddition, enabling efficient catalysis in hydroalcoholic solvents.
• Nickel coupling in water: Ni(phen)₂Br₂ at 2 mol%, with zinc nanopowder and K₃PO₄, couples decanethiol to 4-methoxyiodobenzene in aqueous surfactant solution. Manganese, ascorbic acid and PMHS all fail as the reductant.
• Palladium aerobic oxidation: with palladium(II) it gives water-tolerant, recyclable catalysts for aerobic oxidation of alcohols to aldehydes, ketones and carboxylic acids.
• Redox indicator: with Fe²⁺ it forms ferroin, the most widely used redox indicator in chemistry, absorbing at 510 nm with a molar absorptivity of 11,100 mol⁻¹ dm³ cm⁻¹.
• Ligand specificity: 2,9-dimethyl substitution (neocuproine) impairs the same nickel coupling, and DPPF, DPPE and DPPB give significantly lower yields.

Shipping Destinations

• EU & UK: Priority delivery, 2–5 business days.
• Switzerland (DDP): 3–7 business days, duties and taxes prepaid.