Phenanthroline

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Phenanthroline
Phenanthroline bottle sample.jpg
Phenanthroline monohydrate sample
Names
IUPAC name
1,10-phenanthroline
Other names
4,5-Diazaphenanthrene
O-phenanthroline
Properties
C12H8N2
Molar mass 180.21 g/mol
Appearance Colorless crystalline solid
Density 1.31 g/cm3
Melting point 117 °C (243 °F; 390 K)
Boiling point 300 °C (572 °F; 573 K)
0.269 g/100 ml (at 25 °C)
Solubility Soluble in acetone, ethanol
Acidity (pKa) 4.86 (phenH+)
Hazards
Safety data sheet AcrosOrganics
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phenanthroline or 1,10-phenanthroline is a heterocyclic organic compound, used as a ligand in coordination chemistry, as it forms strong complexes with many metal ions.

Properties

Chemical

Addition of phenanthroline to iron(III) sulfate in water gives ferroin.

3 1,10-Phen + Fe2+ → [Fe(1,10-Phen)3]2+

Physical

Phenanthroline is a white solid, poorly soluble in water, but more soluble in organic solvents, such as primary alcohols and acetone.

Availability

Can be purchased online.

Preparation

Can be made by two successive Skraup reactions of glycerol with o-phenylenediamine, catalyzed by conc. sulfuric acid, and a selective oxidizing agent, such as aqueous arsenic acid or nitrobenzene. Dehydration of glycerol gives acrolein, which condenses with the amine followed by a cyclization.

Projects

  • Make ferroin
  • Belousov–Zhabotinsky reaction
  • Alkyllithium reagent indicator

Handling

Safety

Phenanthroline is irritant and harmful. It is considered a mild neurotoxin, strong nephrotoxin, and powerful diuretic.

Storage

In closed bottles, away from corrosive vapors.

Disposal

Can be destroyed with a strong oxidizer, like Fenton's reagent or piranha solution by slowly adding it in the oxidizing mixture, followed by neutralization and then poured down the drain.

References

Relevant Sciencemadness threads