7214. o-Phenanthroline

Nomenclature

CAS number: 66-71-7
1,10-Phenanthroline; 4,5-phenanthroline.
C12H8N2; mol wt 180.21.
C 79.98%, H 4.47%, N 15.54%.

Description and references

Metal chelator. Prepn: F. Blau, Monatsh. Chem. 19, 666 (1898); K. Madeja, J. Prakt. Chem. 17, 104 (1962). Solubilities: J. Burgess, R. I. Haines, J. Chem. Eng. Data 23, 196 (1978). Crystal and molecular structure: S. Nishigaki et al., Acta Crystallogr. B34, 875 (1978). Review of analytical uses: F. Vydra, M. Kopanica, Chemist-Analyst 52, 88-94 (1963); of chemistry and reactivity: L. A. Summers, Adv. Heterocycl. Chem. 22, 1-69 (1978); W. Sliwa, Heterocycles 12, 1207-1237 (1979); P. G. Sammes, G. Yahioglu, Chem. Soc. Rev. 1994, 327-334; of chiral derivatives used in asymmetric catalysis: E. Schoffers, Eur. J. Org. Chem. 2003, 1145-1152.

Chemical structure

Properties

White, cryst powder. mp 117°. pKa1: 4.8-5.2. uv max (water): 265 nm (ε 29510). Soly at 298.2 K (mol/dm3): water 0.0149; ethanol 2.78.

Derivative

Monohydrate.

Nomenclature

CAS number: 5144-89-8
C12H8N2.H2O; mol wt 198.22.
C 72.71%, H 5.08%, N 14.13%, O 8.07%.

Use

As an analytical reagent for determn of metals in chemical and biological systems through complex formation. Colorimetric indicator; indicator (“Ferroin”) in combination with ferrous ions for oxidation/reduction reactions. In organic syntheses as an activator.