10272. PAN

Nomenclature

CAS number: 85-85-8
1-[2-(2-Pyridinyl)diazenyl]-2-naphthalenol; 1-(2-pyridinylazo)-2-naphthalenol; 1-(2-pyridylazo)-2-naphthol.
C15H11N3O; mol wt 249.27.
C 72.28%, H 4.45%, N 16.86%, O 6.42%.

Description and references

Cation chelant; reacts with metal ions to form stable, intensely colored complexes. Prepn: A. Tschitschibabin, M. Rjasanzew, Chem. Zentralbl. 1916, III, 228. Improved synthesis: S. Wiejak et al., Pol. J. Chem. 58, 895 (1984). Spectroscopy studies of PAN and its metal chelates: D. Betteridge, D. John, Analyst 98, 377, 390 (1973) DOI. Electronic absorption spectra: M. S. Masoud, H. H. Hammud, Spectrochim. Acta A 57, 977 (2001) DOI PubMed. Metal ion extraction applications: J. Gao et al., Talanta 40, 195 (1993) DOI; I. Narin, M. Soylak, ibid. 60, 215 (2003) DOI; M. Tuzen et al., Anal. Lett. 37, 473 (2004) DOI.

Chemical structure

Properties

Orange-red solid, mp 140-141°. Irritant. Absorption max (diethyl ether): 458 nm; (acetone): 463 nm; (DMSO): 471 nm; (acetonitrile): 462 nm; (ethanol): 465 nm; (methanol): 465 nm. Metal complexes insol in water.

Use

Chromogenic indicator for complexometric and spectrophotometric detection of metal ions. In extraction of metal ions. In ion chromatography applications.