Molybdocene dichloride

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/c2*1-2-4-5-3-1;;;/h2*1-5H;2*1H;/q2*-1;;;+2/p-2
Key: QGGWSCVAFKWITK-UHFFFAOYSA-L
InChI=1/2C5H5.2ClH.Mo/c2*1-2-4-5-3-1;;;/h2*1-5H;2*1H;/q2*-1;;;+2/p-2/r2C5H5.Cl2Mo/c2*1-2-4-5-3-1;1-3-2/h2*1-5H;/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)

^[1]

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.