3347. 2,2′-Bipyridine

Nomenclature

CAS number: 366-18-7
2,2′-Bipyridyl; α,α′-dipyridyl; CI-588.
C10H8N2; mol wt 156.18.
C 76.90%, H 5.16%, N 17.94%.

Description and references

Bidentate metal chelating ligand. Prepn from pyridine: H. Meyer, A. Hofmann-Meyer, J. Prakt. Chem. Chem.-Ztg. 102, 287 (1921); C. R. Smith, J. Am. Chem. Soc. 46, 414 (1924); using Raney Ni: W. H. F. Sasse, Org. Synth. coll. vol. V, 102 (1973). Manuf: P. F. H. Freeman, R. Ghosh, US 2962502 (1960 to I.C.I.). Absorption spectrum: P. Krumholz, J. Am. Chem. Soc. 73, 3487 (1951). Crystal structure: L. L. Merritt, Jr., E. D. Schroeder, Acta Crystallogr. 9, 801 (1956). Pharmacologic study: P. Bass et al., J. Pharmacol. Exp. Ther. 152, 104 (1966). Review of chemistry of complex formation: E. K"onig, Coord. Chem. Rev. 3, 471-495 (1968); of properties of metal complexes: G. Nord, Comments Inorg. Chem. 4, 193-212 (1985); of ligands containing multiple 2,2′-bipyridine units: C. Kaes et al., Chem. Rev. 100, 3553-3590 (2000); of synthesis methods: G. R. Newkome et al., Eur. J. Org. Chem. 2004, 235-254.

Chemical structure

Properties

Crystals from petroleum ether, mp 70-71°. bp 272-273°. d 1.28. Poisonous. uv max (water): 233, 280 nm (ε 10200, 13300). Soly in water (mg/ml): 6.4; in 0.1 N HCl: 25.7. Insol in sodium hydroxide. Very sol in alcohol, ether, benzene, chloroform, petr ether. LD50 i.p. in mice: 200 mg/kg. See: R. W. Grady et al., J. Pharmacol. Exp. Ther. 196, 478 (1976).

Use

Reagent for the determn of iron. Ligand in coordination chemistry; building block in supramolecular chemistry.