- Vanadocene dichloride
Vanadocene dichloride Identifiers Abbreviations Cp2VCl2 CAS number RTECS number YW1580000 Properties Molecular formula C10H10Cl2V Molar mass 252.03 g/mol Appearance Green solid Density 1.7 g/ml Melting point
Solubility in water Soluble (Hydrolysis) Structure Crystal structure Monoclinic Coordination
Tetrahedral Hazards R-phrases S-phrases Main hazards Irritant NFPA 704 Related compounds Related compounds Titanocene dichloride
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Vanadocene dichloride, dichloro bis(η5-cyclopentadienyl)vanadium(IV) is (η5-C5H5)2VCl2 (commonly abbreviated as Cp2VCl2). It is a structural analoque of titanocene dichloride but with vanadium(IV) instead of titanium(IV). This compound has one unpaired electron, hence Cp2VCl2 is paramagnetic. Vanadocene dichloride is a suitable precursor for variety of bis(cyclopentadienyl)vanadium(IV) compounds.
Reduction of vanadocene dichloride gives vanadocene (C5H5)2V.
Cp2VCl2 was first prepared by Wilkinson and Birmingham via the reaction of NaC5H5 and VCl4 in THF, followed by work up by extraction with chloroform and hydrogen chloride and recrystallization from toluene.
Like titanocene dichloride, this organovanadium compound is currently being investigated as a potential anticancer drug (currently in clinical trials). The mechanism by which it acts is not understood, but some conjecture that it might be due to its interactions with the protein transferrin.
- ^ G. Wilkinson and J.G. Birmingham (1954). "Bis-cyclopentadienyl Compounds of Ti, Zr, V, Nb and Ta". Journal of the American Chemical Society 76 (17): 4281–4284. doi:10.1021/ja01646a008.
- ^ Murthy M. S., Rao L. N., Kuo L. Y., Toney J. H., Marks T. J. (1988). "Antitumor and toxicologic properties of the organometallic anticancer agent vanadocene dichloride.". Inorg. Chimica Acta 152 (2): 117–124. doi:10.1016/S0020-1693(00)83343-5.
- T. Hirao, A. Ogawa, M. Asahara, Y. Muguruma, H. Sakurai (2005), "d,l-Selective Pinacol-Type Coupling Using Zinc, Chlorosilane, and Catalytic Amount of Cp2VCl2; dl-1,2-Dicyclohexylethanediol", Org. Synth. 81: 26, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v81p0026
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