Phenanthroline

Phenanthroline (phen) is a heterocyclic organic compound. It is a white solid that is soluble in organic solvents. It is used widely as a chelating agent and an indicator. Its name is derived from the parent compound phenanthrene.

Structure and properties

Phenanthroline is a tricyclic compound and a bipyridine, consisting of two pyridyl rings bridged by a 2,9-diazabicyclo[6.6.2]decane group. The molecule is flat and approximately rectangular, the dimensions of the rectangle being 1.10 × 0.67 nm.

Synthesis

Phenanthroline may be prepared by two successive Skraup reactions of glycerol with o-phenylenediamine, catalyzed by sulfuric acid, and dehydrating the resulting tetrahydrophenanthroline with zinc dust and acetic acid.

Uses

Phenanthroline is a widely used ligand in coordination chemistry. It forms strong complexes with most metal ions. In these complexes, phenanthroline is neutral and acts as a tridentate ligand.

Safety

Phenanthroline can cause irritation to the skin and eyes. It is harmful if swallowed or inhaled.

See also

• Bipyridine
• Phenanthrene
• Chelation

References

Phenanthroline Resources
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