10306. Salicylaldehyde Phenylhydrazone

Nomenclature

CAS number: 614-65-3
2-Hydroxybenzaldehyde 2-phenylhydrazone; salicylic aldehyde phenylhydrazone.
C13H12N2O; mol wt 212.25.
C 73.56%, H 5.70%, N 13.20%, O 7.54%.

Description and references

Indicator used for the titration of Grignard, organolithium, and hydridic reagents. Prepn from salicylaldehyde and phenylhydrazine: E. Fischer, Ber. 17, 572 (1884); A. Rssing, ibid. 2988. Formation mechanism and kinetics: M. P. Bastos et al., J. Org. Chem. 46, 3342 (1981) DOI. Spectroscopy studies: M. H. M. Abou-El-Wafa, U. M. Rabie, Rev. Roum. Chim. 46, 723 (2001); H. H. Hammud et al., Spectrochim. Acta A 63, 255 (2006) DOI PubMed. Polarography studies: V. Krishnaswamy, M. Anbu, Acta Cienc. Indica Chem. 17C, 387 (1991). Tautomerism: G. N. Ledesma et al., J. Mol. Struct. 415, 115 (1997) DOI; and metal coordination properties: idem et al., Polyhedron 17, 1517 (1998) DOI; G. A. Ibaez et al., J. Mol. Struct. 605, 17 (2002) DOI. Metal chelate studies: P. Umpathy et al., Indian J. Chem. 3, 471 (1965); N. Thankarajan, K. P. Kumar, ibid. 30A, 646 (1991); eidem, J. Indian Chem. Soc. 69, 780 (1992). Organometallic reagent titrations: B. E. Love, E. G. Jones, J. Org. Chem. 64, 3755 (1999) DOI PubMed.

Chemical structure

Properties

Needles, mp 142-143°. bp28 234°. pKa (50% ethanol): 12.38. Absorption max in acetonitrile: 299, 343 nm (ε 10480, 29060); in chloroform: 303, 346 nm (ε 10720, 22240); in DMF: 303, 352 nm (ε 10720, 25360); in methanol: 303, 346 nm (ε 10840, 24470); in ethanol: 300, 348 nm (ε 7350, 15080); in 50% ethanol (neutral form): 348 nm; in 50% ethanol (ionic form): 370 nm. Emission: 435 nm.

Use

Titration indicator for organometallic reagents. Gravimetric reagent for palladium. Also for separation and determn of lanthanum.