Titanocene dicarbonyl

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Titanocene dicarbonyl
IUPAC name
Other names
3D model (JSmol)
PubChem CID
  • InChI=1S/2C5H5.2CO.Ti/c2*1-2-4-5-3-1;2*1-2;/h2*1-3H,4H2;;;/q2*-1;;;
  • C1C=CC=[C-]1.C1C=CC=[C-]1.C(=O)=[Ti]=C=O
Molar mass 234.09 g/mol
Appearancemaroon solid pyrophoric
Melting point 90 °C (194 °F; 363 K)
Boiling point Sublimes at40 to 80 °C (104 to 176 °F; 313 to 353 K)at 0.001 mmHg
Solubility in other solvents THF, benzene
Occupational safety and health (OHS/OSH):
Main hazards
Related compounds
Related compounds
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

Dicarbonylbis(cyclopentadienyl)titanium is the chemical compound with the formula (η5-C5H5)2Ti(CO)2, abbreviated Cp2Ti(CO)2. This maroon-coloured, air-sensitive species is soluble in aliphatic and aromatic solvents. [1] It has been used for the deoxygenation of sulfoxides, reductive coupling of aromatic aldehydes and reduction of aldehydes.

Structure and synthesis

Cp2Ti(CO)2 is prepared by the reduction of titanocene dichloride with magnesium as a slurry in THT under an atmosphere of carbon monoxide. [2]

(C5H5)2TiCl2 + Mg + 2 CO → (C5H5)2Ti(CO)2 + MgCl2

Both Cp2Ti(CO)2 and Cp2TiCl2 are tetrahedral as are related zirconium and hafnium compounds. Of historical interest, the complex was first prepared by the reduction of titanocene dichloride with sodium cyclopentadienyl under an atmosphere of carbon monoxide. [3]

Its structure has been confirmed by X-ray crystallography. [4]

Related Research Articles


A metallocene is a compound typically consisting of two cyclopentadienyl anions (C
, abbreviated Cp) bound to a metal center (M) in the oxidation state II, with the resulting general formula (C5H5)2M. Closely related to the metallocenes are the metallocene derivatives, e.g. titanocene dichloride, vanadocene dichloride. Certain metallocenes and their derivatives exhibit catalytic properties, although metallocenes are rarely used industrially. Cationic group 4 metallocene derivatives related to [Cp2ZrCH3]+ catalyze olefin polymerization.

Titanium tetrachloride Inorganic chemical compound

Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide (TiO2) and hydrochloric acid, a reaction formerly exploited to produce fake smoke on film sets. It is sometimes referred to as "tickle" or "tickle 4" due to the phonetic resemblance of its molecular formula (TiCl4) to the word.

Titanocene dichloride Chemical compound

Titanocene dichloride is the organotitanium compound with the formula (η5-C5H5)2TiCl2, commonly abbreviated as Cp2TiCl2. This metallocene is a common reagent in organometallic and organic synthesis. It exists as a bright red solid that slowly hydrolyzes in air. It shows antitumour activity and was the first non-platinum complex to undergo clinical trials as a chemotherapy drug.

Tebbes reagent Chemical compound

Tebbe's reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2. It is used in the methylenation of carbonyl compounds, that is it converts organic compounds containing the R2C=O group into the related R2C=CH2 derivative. It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research.

Petasis reagent Chemical compound

The Petasis reagent, named after Nicos A. Petasis, is an organotitanium compound with the formula Cp2Ti(CH3)2. It is an orange-colored solid.

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.

Organotitanium compound

Organotitanium compounds in organometallic chemistry contain carbon-titanium chemical bonds. Organotitanium chemistry is the science of organotitanium compounds describing their physical properties, synthesis and reactions. They are reagents in organic chemistry and are involved in major industrial processes.

Niobocene dichloride is the organometallic compound with the formula (C5H5)2NbCl2, abbreviated Cp2NbCl2. This paramagnetic brown solid is a starting reagent for the synthesis of other organoniobium compounds. The compound adopts a pseudotetrahedral structure with two cyclopentadienyl and two chloride substituents attached to the metal. A variety of similar compounds are known, including Cp2TiCl2.

Organozirconium chemistry

Organozirconium compounds are organometallic compounds containing a carbon to zirconium chemical bond. Organozirconium chemistry is the corresponding science exploring properties, structure, and reactivity of these compounds. Organozirconium compounds have been widely studied, in part because they are useful catalysts in Ziegler-Natta polymerization.

Sodium cyclopentadienide Chemical compound

Sodium cyclopentadienide is an organosodium compound with the formula C5H5Na. The compound is often abbreviated as NaCp, where Cp is the cyclopentadienide anion. Sodium cyclopentadienide is a colorless solid, although samples often are pink owing to traces of oxidized impurities.

Organoiron chemistry is the chemistry of iron compounds containing a carbon-to-iron chemical bond. Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrate. While iron adopts oxidation states from Fe(−II) through to Fe(VII), Fe(IV) is the highest established oxidation state for organoiron species. Although iron is generally less active in many catalytic applications, it is less expensive and "greener" than other metals. Organoiron compounds feature a wide range of ligands that support the Fe-C bond; as with other organometals, these supporting ligands prominently include phosphines, carbon monoxide, and cyclopentadienyl, but hard ligands such as amines are employed as well.

Organovanadium chemistry is the chemistry of organometallic compounds containing a carbon to vanadium (V) chemical bond. Organovanadium compounds find only minor use as reagents in organic synthesis but are significant for polymer chemistry as catalysts.

In organometallic chemistry, bent metallocenes are a subset of metallocenes. In bent metallocenes, the ring systems coordinated to the metal are not parallel, but are tilted at an angle. A common example of a bent metallocene is Cp2TiCl2. Several reagents and much research is based on bent metallocenes.

Vanadocene Chemical compound

Vanadocene, bis(η5-cyclopentadienyl) vanadium, is the organometallic compound with the formula V(C5H5)2, commonly abbreviated Cp2V. It is a violet crystalline, paramagnetic solid. Vanadocene has relatively limited practical use, but it has been extensively studied.

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.

Titanocene pentasulfide Chemical compound

Titanocene pentasulfide is the organotitanium compound with the formula (C5H5)2TiS5, commonly abbreviated as Cp2TiS5. This metallocene exists as a bright red solid that is soluble in organic solvents. It is of academic interest as a precursor to unusual allotropes of elemental sulfur as well as some related inorganic rings.

Bis(cyclopentadienyl)titanium(III) chloride Chemical compound

Bis(cyclopentadienyl)titanium(III) chloride, also known as the Nugent–RajanBabu reagent, is the organotitanium compound which exists as a dimer with the formula [(C5H5)2TiCl]2. It is an air sensitive green solid. The complex finds specialized use in synthetic organic chemistry as a single electron reductant.

Magnesocene, also known as bis(cyclopentadienyl)magnesium(II) and sometimes abbreviated as MgCp2, is an organometallic compound with the formula Mg(η5-C5H5)2. It is an example of an s-block main group sandwich compound, structurally related to the d-block element metallocenes, and consists of a central magnesium atom sandwiched between two cyclopentadienyl rings.

(Cyclopentadienyl)titanium trichloride Chemical compound

(Cyclopentadienyl)titanium trichloride is an organotitanium compound with the formula (C5H5)TiCl3. It is a moisture sensitive orange solid. The compound adopts a piano stool geometry.

Decamethyltitanocene dichloride Chemical compound

Decamethyltitanocene dichloride is an organotitanium compound with the formula Cp*2TiCl2 (where Cp* is C5(CH3)5, derived from pentamethylcyclopentadiene). It is a red solid that is soluble in nonpolar organic solvents. The complex has been the subject of extensive research. It is a precursor to many other organotitanium complexes


  1. Sikora, D. J.; Moriarty, K. J.; Rausch, M. D. (1990). Reagents for Transition Metal complex and Organometallic syntheses. Inorganic Syntheses. Vol. 28. pp. 250–251. doi:10.1002/9780470132593.ch64.
  2. Snead, Thomas E. (2001). "Dicarbonylbis(cyclopentadienyl)titanium". Encyclopedia of Reagents for Organic Synthesis . John Wiley & Sons, Ltd. doi:10.1002/047084289X.rd073. ISBN   0471936235.
  3. Murray, James G. (1959). "A Metal Carbonyl Compound of Titanium". Journal of the American Chemical Society. 81 (3): 752–753. doi:10.1021/ja01512a062.
  4. Atwood, Jerry L.; Stone, Karen E.; Alt, Helmut G.; Hrncir, Duane C.; Rausch, Marvin D. (1975). "Crystal and Molecular Structure of Titanocene Dicarbonyl, (η5-C5H5)2Ti(CO)2". Journal of Organometallic Chemistry. 96: C4–C6. doi:10.1016/S0022-328X(00)86431-1.