Vanadocene dichloride

Vanadocene dichloride
Names
	IUPAC name Dichlorobis(η5-cyclopentadienyl) vanadium
	Other names Dicyclopentadienyl vanadium dichloride
Identifiers
CAS Number	12083-48-6 ;
3D model (JSmol)	Interactive image;
Abbreviations	Cp2VCl2
ECHA InfoCard	100.031.943
PubChem CID	82917;
RTECS number	YW1580000;
UNII	4W2E0IDO21 ;
CompTox Dashboard (EPA)	DTXSID2024616 ;
	SMILES c1ccc[cH-]1.c2ccc[cH-]2.[V+4].[Cl-].[Cl-];
Properties
Chemical formula	C10H10Cl2V
Molar mass	252.03 g/mol
Appearance	Green solid
Density	1.7 g/ml
Melting point	decomposes
Boiling point	decomposes
Solubility in water	Soluble (Hydrolysis)
Structure
Crystal structure	Monoclinic
Coordination geometry	Tetrahedral
Hazards
Main hazards	Irritant
R-phrases (outdated)	R25 R36/37/38 R38
S-phrases (outdated)	S26 S28 S36/37/39 S45
NFPA 704 (fire diamond)	0 2 1
Related compounds
Related compounds	Titanocene dichloride; Zirconocene dichloride; Hafnocene dichloride; Niobocene dichloride; Tanatalocene dichloride; Molybdenocene dichloride; Tungstenocene dichloride
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Vanadocene dichloride is an organometallic complex with formula (η⁵-C₅H₅)₂VCl₂ (commonly abbreviated as Cp₂VCl₂). It is a structural analogue 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.

Preparation

Cp₂VCl₂ was first prepared by Wilkinson and Birmingham via the reaction of NaC₅H₅ and VCl₄ in THF.[1]

Reactions and use

The compound has been used in organic synthesis.[2]

Reduction of vanadocene dichloride gives vanadocene, (C₅H₅)₂V.

Like titanocene dichloride, this organovanadium compound was investigated as a potential anticancer drug. It was conjectured to function by interactions with the protein transferrin.[3]

References

Wilkinson, G.; Birmingham, J. G. (1954). "Bis-cyclopentadienyl Compounds of Ti, Zr, V, Nb and Ta". J. Am. Chem. Soc. 76 (17): 4281–4284. doi:10.1021/ja01646a008.
Hirao, T.; Ogawa, A.; Asahara, M.; Muguruma, Y.; Sakurai, H. (2005). "d,l-Selective Pinacol-Type Coupling Using Zinc, Chlorosilane, and Catalytic Amount of Cp₂VCl₂; dl-1,2-Dicyclohexylethanediol". Organic Syntheses. 81: 26.
Honzíček, Jan; Vinklárek, Jaromír (2015). "Bioinorganic chemistry of vanadocene dichloride". Inorganica Chimica Acta. 437: 87–94. doi:10.1016/j.ica.2015.08.008.

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[wilkinson-1] Wilkinson, G.; Birmingham, J. G. (1954). "Bis-cyclopentadienyl Compounds of Ti, Zr, V, Nb and Ta". J. Am. Chem. Soc. 76 (17): 4281–4284. doi:10.1021/ja01646a008.

[2] Hirao, T.; Ogawa, A.; Asahara, M.; Muguruma, Y.; Sakurai, H. (2005). "d,l-Selective Pinacol-Type Coupling Using Zinc, Chlorosilane, and Catalytic Amount of Cp₂VCl₂; dl-1,2-Dicyclohexylethanediol". Organic Syntheses. 81: 26.

[3] Honzíček, Jan; Vinklárek, Jaromír (2015). "Bioinorganic chemistry of vanadocene dichloride". Inorganica Chimica Acta. 437: 87–94. doi:10.1016/j.ica.2015.08.008.