(Pentamethylcyclopentadienyl)titanium trichloride

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(Pentamethylcyclopentadienyl)­titanium trichloride
Cp*TiCl3.svg
Names
Other names
Cp*TiCl3
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.152.688 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UN number 3261
  • InChI=1S/C10H15.3ClH.Ti/c1-6-7(2)9(4)10(5)8(6)3;;;;/h1-5H3;3*1H;/q;;;;+3/p-3
    Key: QCEOZLISXJGWSW-UHFFFAOYSA-K
  • CC1=C([C](C(=C1C)C)C)C.Cl[Ti](Cl)Cl
Properties
C10H15Cl3Ti
Molar mass 289.45 g·mol−1
AppearanceOrange solid
Melting point 225 °C (437 °F; 498 K)
Hazards
GHS labelling: [1]
GHS-pictogram-acid.svg
Danger
H314
P280, P305+P351+P338, P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(Pentamethylcyclopentadienyl)titanium trichloride is an organotitanium compound with the formula Cp*TiCl3 (Cp* = C5(CH3)5). It is an orange solid. The compound adopts a piano stool geometry. An early synthesis involve the combination of lithium pentamethylcyclopentadienide and titanium tetrachloride. [2]

The compound is an intermediate in the synthesis of decamethyltitanocene dichloride. In the presence of organoaluminium compounds and other additives, it catalyzes the polymerization of alkenes. [3] [4]

See also

Related Research Articles

<span class="mw-page-title-main">Metallocene</span>

A metallocene is a compound typically consisting of two cyclopentadienyl anions (C
5
H
5
, 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.

<span class="mw-page-title-main">Cyclopentadienyl complex</span> Coordination complex of a metal and Cp⁻ ions

A cyclopentadienyl complex is a coordination complex of a metal and cyclopentadienyl groups. Cyclopentadienyl ligands almost invariably bind to metals as a pentahapto (η5-) bonding mode. The metal–cyclopentadienyl interaction is typically drawn as a single line from the metal center to the center of the Cp ring.

<span class="mw-page-title-main">Pentamethylcyclopentadiene</span> Chemical compound

1,2,3,4,5-Pentamethylcyclopentadiene is a cyclic diene with the formula C5Me5H (Me = CH3). 1,2,3,4,5-Pentamethylcyclopentadiene is the precursor to the ligand 1,2,3,4,5-pentamethylcyclopentadienyl, which is often denoted Cp* (C5Me5) and read as "C P star", the "star" signifying the five methyl groups radiating from the core of the ligand. In contrast to less-substituted cyclopentadiene derivatives, Cp*H is not prone to dimerization.

<span class="mw-page-title-main">Titanocene dichloride</span> 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.

<span class="mw-page-title-main">Sandwich compound</span> Chemical compound made of two ring ligands bound to a metal

In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic, covalent bonds to two arene (ring) ligands. The arenes have the formula CnHn, substituted derivatives and heterocyclic derivatives. Because the metal is usually situated between the two rings, it is said to be "sandwiched". A special class of sandwich complexes are the metallocenes.

<span class="mw-page-title-main">Organotitanium chemistry</span>

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

<span class="mw-page-title-main">Titanocene dicarbonyl</span> Chemical compound

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. It has been used for the deoxygenation of sulfoxides, reductive coupling of aromatic aldehydes and reduction of aldehydes.

<span class="mw-page-title-main">Group 2 organometallic chemistry</span>

Group 2 organometallic chemistry refers to the chemistry of compounds containing carbon bonded to any group 2 element. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organmetallic group 2 compounds are rare and are typically limited to academic interests.

<span class="mw-page-title-main">Organozirconium chemistry</span>

Organozirconium chemistry is the science of exploring the properties, structure, and reactivity of organozirconium compounds, which are organometallic compounds containing chemical bonds between carbon and zirconium. Organozirconium compounds have been widely studied, in part because they are useful catalysts in Ziegler-Natta polymerization.

<span class="mw-page-title-main">Pentamethylcyclopentadienyl iridium dichloride dimer</span> Chemical compound

Pentamethylcyclopentadienyl iridium dichloride dimer is an organometallic compound with the formula [(C5(CH3)5IrCl2)]2, commonly abbreviated [Cp*IrCl2]2 This bright orange air-stable diamagnetic solid is a reagent in organometallic chemistry.

<span class="mw-page-title-main">Organoscandium chemistry</span> Chemistry of compounds containing a carbon to scandium chemical bond

Organoscandium chemistry is an area with organometallic compounds focused on compounds with at least on carbon to scandium chemical bond. The interest in organoscandium compounds is mostly academic but motivated by potential practical applications in catalysis, especially in polymerization. A common precursor is scandium chloride, especially its THF complex.

<span class="mw-page-title-main">Rhodocene</span> Organometallic chemical compound

Rhodocene is a chemical compound with the formula [Rh(C5H5)2]. Each molecule contains an atom of rhodium bound between two planar aromatic systems of five carbon atoms known as cyclopentadienyl rings in a sandwich arrangement. It is an organometallic compound as it has (haptic) covalent rhodium–carbon bonds. The [Rh(C5H5)2] radical is found above 150 °C (302 °F) or when trapped by cooling to liquid nitrogen temperatures (−196 °C [−321 °F]). At room temperature, pairs of these radicals join via their cyclopentadienyl rings to form a dimer, a yellow solid.

Scandium compounds are compounds containing the element scandium. The chemistry of scandium is almost completely dominated by the trivalent ion, Sc3+, due to its electron configuration, [Ar] 3d14s2. The radii of M3+ ions in the table below indicate that the chemical properties of scandium ions have more in common with yttrium ions than with aluminium ions. In part because of this similarity, scandium is often classified as a lanthanide-like element.

<span class="mw-page-title-main">Bis(cyclopentadienyl)titanium(III) chloride</span> 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.

<span class="mw-page-title-main">Pentamethylcyclopentadienyl rhodium dichloride dimer</span> Chemical compound

Pentamethylcyclopentadienyl rhodium dichloride dimer is an organometallic compound with the formula [(C5(CH3)5RhCl2)]2, commonly abbreviated [Cp*RhCl2]2 This dark red air-stable diamagnetic solid is a reagent in organometallic chemistry.

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.

<span class="mw-page-title-main">(Pentamethylcyclopentadienyl)aluminium(I)</span> Chemical compound

(Pentamethylcyclopentadienyl)aluminium(I) is an organometallic compound with the formula Al(C5Me5) ("Me" is a methyl group; CH3). The compound is often abbreviated to AlCp* or Cp*Al, where Cp* is the pentamethylcyclopentadienide anion (C5Me5). Discovered in 1991 by Dhmeier et al., AlCp* serves as the first ever documented example of a room temperature stable monovalent aluminium compound. In its isolated form, Cp*Al exists as the tetramer [Cp*Al]4, and is a yellow crystal that decomposes at temperatures above 100 °C but also sublimes at temperatures above 140 °C.

<span class="mw-page-title-main">(Cyclopentadienyl)titanium trichloride</span> 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.

<span class="mw-page-title-main">(Cyclopentadienyl)zirconium trichloride</span> Chemical compound

(Cyclopentadienyl)zirconium trichloride is an organozirconium compound with the formula (C5H5)ZrCl3. It a moisture-sensitive white solid. The compound adopts a polymeric structure. The compound has been well studied spectroscopically.

<span class="mw-page-title-main">Decamethyltitanocene dichloride</span> 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 organotitanium complexes. The complex is related to titanocene dichloride, which lacks the methyl groups.

References

  1. "Trichloro(pentamethylcyclopentadienyl)titanium(IV) 446289". Sigma-Aldrich.
  2. King, R.B.; Bisnette, M.B. (1967). "Organometallic chemistry of the transition metals XXI. Some π-pentamethylcyclopentadienyl derivatives of various transition metals". Journal of Organometallic Chemistry. 8 (2): 287–297. doi:10.1016/S0022-328X(00)91042-8.
  3. Ishihara, N.; Kuramoto, M.; Uoi, M. (1988). "Stereospecific polymerization of styrene giving the syndiotactic polymer". Macromolecules. 21 (12): 3356–3360. Bibcode:1988MaMol..21.3356I. doi:10.1021/ma00190a003.
  4. Stephan, Douglas W.; Stewart, Jeffrey C.; Guérin, Frédéric; Courtenay, Silke; Kickham, James; Hollink, Emily; Beddie, Chad; Hoskin, Aaron; Graham, Todd; Wei, Pingrong; Spence, Rupert E. v. H.; Xu, Wei; Koch, Linda; Gao, Xiaoliang; Harrison, Daryll G. (2003). "An Approach to Catalyst Design: Cyclopentadienyl-Titanium Phosphinimide Complexes in Ethylene Polymerization". Organometallics. 22 (9): 1937–1947. doi:10.1021/om020954t.