Molybdocene dichloride

Molybdocene dichloride
source ↗	source ↗
Names
	IUPAC name dichlorobis(η5-cyclopentadienyl)molybdenum(IV)
	Other names molybdocene dichloride,; molybdenocene dichloride,; dichloridobis(cyclopentadienyl)molybdenum(IV)
Identifiers
CAS Number	12184-22-4;
3D model (JSmol)	Interactive image;
ChemSpider	398274;
ECHA InfoCard	100.159.644
PubChem CID	452153;
CompTox Dashboard (EPA)	DTXSID10923978 ;
	InChI InChI=1S/2C5H5.2ClH.Mo/c21-2-4-5-3-1;;;/h21-5H;21H;/q2-1;;;+2/p-2 Key: QGGWSCVAFKWITK-UHFFFAOYSA-L; InChI=1/2C5H5.2ClH.Mo/c21-2-4-5-3-1;;;/h21-5H;21H;/q2-1;;;+2/p-2/r2C5H5.Cl2Mo/c21-2-4-5-3-1;1-3-2/h21-5H;/q2*-1; Key: QGGWSCVAFKWITK-OWLYHJECAX;
	SMILES [cH-]1cccc1.[cH-]1cccc1.Cl[Mo+2]Cl;
Properties
Chemical formula	C10H10Cl2Mo
Molar mass	297.04 g·mol−1
Appearance	greenish-brown powder
Solubility in water	insoluble, moisture sensitive
Hazards
Safety data sheet (SDS)
Related compounds
Related compounds	Ferrocene; Zirconocene dichloride; Vanadocene dichloride; Niobocene dichloride; Titanocene dichloride; Tantalocene dichloride
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Molybdocene dichloride is the organomolybdenum compound with the formula (η⁵-C₅H₅)₂MoCl₂ and IUPAC name dichlorobis(η⁵-cyclopentadienyl)molybdenum(IV), and is commonly abbreviated as Cp₂MoCl₂. It is a brownish-green air- and moisture-sensitive powder. In the research laboratory, it is used to prepare many derivatives.

Preparation and structure

The compound is prepared from molybdocene dihydride by treatment with chloroform:²

(C₅H₅)₂MoH₂ + 2 CHCl₃ → (C₅H₅)₂MoCl₂ + 2 CH₂Cl₂

The compound adopts a "clamshell" structure where the Cp rings are not parallel, the average Cp(centroid)-M-Cp angle being 130.6°. The two chloride ligands are cis, the Cl-Mo-Cl angle of 82° being narrower than in niobocene dichloride (85.6°), which in turn is less than in zirconacene dichloride (92.1°). This trend helped to establish the orientation of the HOMO in this class of complex.³

Uses

Unlike the titanocene and zirconacene derivatives, the molybdocene compounds have yielded no commercial applications.

All metallocene dihalides exhibit some anti-cancer activity,⁴ but these have not yielded useful compounds in the clinic.⁵

References

"42-0100 Molybdenum " Bis(cyclopentadienyl)molybdenum dichloride, 99%". Strem Chemicals. 27 July 2011. Retrieved 5 February 2012.
Silavwe, Ned D.; Castellani, Michael P.; Tyler, David R. (1992). "Bis(η5-Cyclopentadienyl)Molybdenum(IV) Complexes". Inorganic Syntheses. Vol. 29. pp. 204–211. doi:10.1002/9780470132609.ch50. ISBN 9780470132609.
K. Prout, T. S. Cameron, R. A. Forder, and in parts S. R. Critchley, B. Denton and G. V. Rees "The crystal and molecular structures of bent bis-π‑cyclopentadienyl-metal complexes: (a) bis-π‑cyclopentadienyldibromorhenium(V) tetrafluoroborate, (b) bis-π‑cyclopentadienyldichloromolybdenum(IV), (c) bis-π‑cyclopentadienylhydroxomethylaminomolybdenum(IV) hexafluorophosphate, (d) bis-π‑cyclopentadienylethylchloromolybdenum(IV), (e) bis-π‑cyclopentadienyldichloroniobium(IV), (f) bis-π‑cyclopentadienyldichloromolybdenum(V) tetrafluoroborate, (g) μ‑oxo-bis[bis-π‑cyclopentadienylchloroniobium(IV)] tetrafluoroborate, (h) bis-π‑cyclopentadienyldichlorozirconium" Acta Crystallogr. 1974, volume B30, pp. 2290–2304. doi:10.1107/S0567740874007011
Roat-Malone, R. M. (2007). Bioinorganic Chemistry: A Short Course (2nd ed.). John Wiley & Sons. pp. 19–20. ISBN 978-0-471-76113-6.
Waern, J. B.; Dillon, C. T.; Harding, M. M. (2005). "Organometallic Anticancer Agents: Cellular Uptake and Cytotoxicity Studies on Thiol Derivatives of the Antitumor Agent Molybdocene Dichloride". J. Med. Chem. 48 (6): 2093–2099. doi:10.1021/jm049585o. PMID 15771451.

[MSDS-1] "42-0100 Molybdenum " Bis(cyclopentadienyl)molybdenum dichloride, 99%". Strem Chemicals. 27 July 2011. Retrieved 5 February 2012.

[2] Silavwe, Ned D.; Castellani, Michael P.; Tyler, David R. (1992). "Bis(η5-Cyclopentadienyl)Molybdenum(IV) Complexes". Inorganic Syntheses. Vol. 29. pp. 204–211. doi:10.1002/9780470132609.ch50. ISBN 9780470132609.

[3] K. Prout, T. S. Cameron, R. A. Forder, and in parts S. R. Critchley, B. Denton and G. V. Rees "The crystal and molecular structures of bent bis-π‑cyclopentadienyl-metal complexes: (a) bis-π‑cyclopentadienyldibromorhenium(V) tetrafluoroborate, (b) bis-π‑cyclopentadienyldichloromolybdenum(IV), (c) bis-π‑cyclopentadienylhydroxomethylaminomolybdenum(IV) hexafluorophosphate, (d) bis-π‑cyclopentadienylethylchloromolybdenum(IV), (e) bis-π‑cyclopentadienyldichloroniobium(IV), (f) bis-π‑cyclopentadienyldichloromolybdenum(V) tetrafluoroborate, (g) μ‑oxo-bis[bis-π‑cyclopentadienylchloroniobium(IV)] tetrafluoroborate, (h) bis-π‑cyclopentadienyldichlorozirconium" Acta Crystallogr. 1974, volume B30, pp. 2290–2304. doi:10.1107/S0567740874007011

[anti-cancer-4] Roat-Malone, R. M. (2007). Bioinorganic Chemistry: A Short Course (2nd ed.). John Wiley & Sons. pp. 19–20. ISBN 978-0-471-76113-6.

[5] Waern, J. B.; Dillon, C. T.; Harding, M. M. (2005). "Organometallic Anticancer Agents: Cellular Uptake and Cytotoxicity Studies on Thiol Derivatives of the Antitumor Agent Molybdocene Dichloride". J. Med. Chem. 48 (6): 2093–2099. doi:10.1021/jm049585o. PMID 15771451.

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