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
EC Number	235-150-8;
PubChem CID	82917;
RTECS number	YW1580000;
UNII	4W2E0IDO21 ;
UN number	3285
CompTox Dashboard (EPA)	DTXSID2024616 ;
	SMILES [cH-]1cccc1.[cH-]1cccc1.Cl[V+2]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
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 0 1
Related compounds
Related compounds	Titanocene dichloride; Zirconocene dichloride; Hafnocene dichloride; Niobocene dichloride; Tantalocene 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). verify (what is ?) 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.

[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.

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