Vanadocene dichloride
From Wikipedia, the free encyclopedia
| Vanadocene dichloride | |
|---|---|
 |
 |
| IUPAC name | dichloridobis(η5-cyclopentadienyl)vanadium |
| Other names | Dicyclopentadienyl vanadium dichloride |
| Identifiers | |
| Abbreviations | Cp2VCl2 |
| CAS number | [12083-48-6] |
| RTECS number | YW1580000 |
| Properties | |
| Molecular formula | C10H10Cl2V |
| Molar mass | 252.03 g/mol |
| Appearance | Green solid |
| Boiling point |
Decomp. |
| Solubility in water | Insoluble |
| Structure | |
| Crystal structure | Triclinic |
| Coordination geometry |
Tetrahedral |
| Hazards | |
| Main hazards | Irritant |
| NFPA 704 |
 0
2
1
|
| R-phrases | R25 R36/37/38 R38 |
| S-phrases | S26 S28 S36/37/39 S45 |
| Related compounds | |
| Related compounds | Titanocene dichloride |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Vanadocene dichloride, dichlorobis(η5-2,4-cyclopentadien-1-yl) vanadium, or dicyclopentadienyl vanadium dichloride is (η5-C5H5)2VCl2 (commonly abbreviated as Cp2VCl2). It is a close relative of titanocene dichloride but with one additional valence electron, hence Cp2VCl2 is paramagnetic. Vanadocene dichloride is a useful precursor to other (C5H5)2V compounds.
Contents |
[edit] Preparation
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.[1]
[edit] Structure
Like its Ti analogue, vanadocene dichloride 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.[2]
[edit] References
- ^ 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:.
- ^ 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: 117–124. doi:.
[edit] Further reading
- 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.
