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Vanadocene dichloride



Vanadocene dichloride
IUPAC name Dicholorobis(η5-2,4-cyclopentadien-1-yl) 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

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.

Additional recommended knowledge

Contents

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]

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]

References

  1. ^ 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.
  2. ^ 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.

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. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Vanadocene_dichloride". A list of authors is available in Wikipedia.
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