132510-07-7

Basic information

• Product Name: Diphenylmethylidene(cyclopentadienyl)(9-fluorenyl)zirconium dichloride
• Synonyms: DIPHENYLMETHYLIDENE(CYCLOPENTADIENYL)(9-FLUORENYL)ZIRCONIUM DICHLORIDE;DIPHENYLMETHYLIDENE(CYCLOPENTADIENYL)(9-FLUORENYL)ZIRCONIUM(IV) DICHLORIDE
• CAS NO: 132510-07-7
• Molecular Formula: C₃₁H₂₂Cl₂Zr
• Molecular Weight: 556.64
• Mol File: 132510-07-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Diphenylmethylidene(cyclopentadienyl)(9-fluorenyl)zirconium dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenylmethylidene(cyclopentadienyl)(9-fluorenyl)zirconium dichloride(132510-07-7)
• EPA Substance Registry System: Diphenylmethylidene(cyclopentadienyl)(9-fluorenyl)zirconium dichloride(132510-07-7)

Safety Data

• Hazardous Substances Data: 132510-07-7(Hazardous Substances Data)

Usage

Description

Diphenylmethylidene(cyclopentadienyl)(9-fluorenyl)zirconium dichloride is an organometallic compound characterized by its unique structure, which consists of a diphenylmethylidene group, a cyclopentadienyl group, a 9-fluorenyl group, and two chlorine atoms bonded to a zirconium atom. This complex structure endows the compound with specific properties that make it suitable for various applications in the field of chemistry.

Uses

Used in Chemical Synthesis:
Diphenylmethylidene(cyclopentadienyl)(9-fluorenyl)zirconium dichloride is used as a catalyst for organic synthesis due to its ability to facilitate and enhance the rate of chemical reactions. Its unique structure allows it to interact with a wide range of organic substrates, making it a versatile catalyst for various types of reactions, such as polymerization, hydroformylation, and olefin metathesis.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Diphenylmethylidene(cyclopentadienyl)(9-fluorenyl)zirconium dichloride is used as a catalyst for the synthesis of complex organic molecules, which are often the active ingredients in various drugs. Its ability to promote selective reactions and improve reaction yields makes it a valuable tool in the development of new pharmaceutical compounds.
Used in Materials Science:
Diphenylmethylidene(cyclopentadienyl)(9-fluorenyl)zirconium dichloride is also utilized in the field of materials science, where it serves as a catalyst for the synthesis of advanced materials with specific properties. These materials can be used in various applications, such as electronics, aerospace, and automotive industries, where high-performance materials are required.
Used in Environmental Applications:
The compound can be employed in environmental applications, such as the catalytic conversion of pollutants and the synthesis of environmentally friendly materials. Its catalytic properties enable the efficient transformation of harmful substances into less toxic or more easily degradable compounds, contributing to a cleaner and more sustainable environment.

storage

1. Store in a cool, ventilated warehouse, away from fire and heat sources.2. It should be stored separately from oxidants and edible chemicals, and mixed storage is prohibited.3. Prohibit the use of equipment and tools that are prone to sparks.

Synthetic route

1-cyclopentadienyl-1-fluorenyl-1,1-diphenylmethane dilithium + zirconium(IV) chloride (10026-11-6) → isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7)

Conditions	Yield
In petroleum ether ZrCl4 was added to Li-compound, petroleum ether was condensed at -78°C, cold bath are removed, 24 h (Ar or N2); extd. in a cellulose extn. thimble with CH2Cl2 overnight, reduced in vol., ppt. was dried in vac.; elem. anal.;	22.1%

zirconium(IV) chloride (10026-11-6) + 9-(Cyclopenta-2,4-dienyl-diphenyl-methyl)-9H-fluorene (132686-51-2) → isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7)

Conditions	Yield
With n-butyllithium In diethyl ether; hexane 2 M C4H9Li in hexane added dropwise at -78°C to soln. of (C13H9)C(C6H5)2(C5H5) (2.2 mmol) in ether, stirred overnight, ZrCl4 (2.2 mmol) added, stirred for 8 h at room temp.; evapd. to dryness, recrystd. (toluene);

isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7) + methylmagnesium bromide (75-16-1) → [((phenyl)2C(C5H4)(fluorenyl(1-)))Zr(methyl)2] (144772-00-9)

Conditions	Yield
In not given	96%

isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7) + α-lithioisopropyl isobutyrate → [(diphenylmethylene(η5-cyclopentadienyl)(η5-9-fluorenyl))Zr(OC(OiPr)CMe2)2] (1008161-96-3)

Conditions	Yield
In not given	92%

isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7) + 2-methylpropylmagnesium chloride (5674-02-2) → (C6H5)2C(C5H4)(C13H8)ZrCl(C4H9) (460325-45-5)

Conditions	Yield
In tetrahydrofuran byproducts: MgCl2; under Ar; mixt. of solns. reacted at 0°C; warmed to room temp.; stirred for 6 h; solvent removed under vac.; washed 3 times (diethyl ether); volatiles removed under vac.; dissolved in n-hexane; filtered off; solvent removed in dried under vac.; detd. by NMR;	10.8%

isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7) → Ph2C(cyclopentadienyl)(fluorenyl)ZrClMe (920298-61-9)

Conditions	Yield
With polymethylalumoxane In toluene Zr complex and polymethylalumoxane in toluene (molar ratio Al/Zr varied from 10 to 3000); not isolated; monitored by UV-spectroscopy;

isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7) + triisobutylaluminum (100-99-2) → (C6H5)2C(C5H4)(C13H8)ZrCl(C4H9) (460325-45-5)

Conditions	Yield
In benzene-d6 byproducts: Al(C4H9)2Cl; under Ar; mixt. of solns. reacted at 20°C at various Al/Zr ratios(10 - 50); or at 80°C at Al/Zr = 10; not isolated; detd. by NMR;

isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7) + triisobutylaluminum (100-99-2) + N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate → [Ph2C(C5H4)(C13H8)Zr-μ-H-.mu-(C4H7)-Al(isobutyl)2][B(C6F5)4]*aluminum-triisobutyl

Conditions	Yield
In benzene-d6 byproducts: PhNMe2, iso-butane, iso-butene; under Ar; mixt. of Zr-complex and Al(iso-Bu)3 solns. stirred for 30 min,heated to 60°C; soln. of (PhNMe2h)(B(C6F5)4) added; after 10 min cooled to room temp.; pptd.; ppt. washed 3 times (C6D6);

isopropylidene-2-(2-methylindenyl)-2-(3-tert-butylcyclopentadienyl)zirconium dichloride (132510-07-7) + methylmagnesium chloride (676-58-4) → [((phenyl)2C(C5H4)(fluorenyl(1-)))Zr(methyl)2] (144772-00-9)

Conditions	Yield
In tetrahydrofuran; diethyl ether in glovebox zirconocene added to flask and dissolved in diethyl ether, added by syringe soln. (THF) of CH3MgCl, attached swivel frit app., stirred at room temp. for 3 d, filtered, filtrate concd., cooled to 0°C, filtered off, dried (vac.);

Upstream product

• 10026-11-6 zirconium(IV) chloride 
• 132686-51-2 9-(Cyclopenta-2,4-dienyl-diphenyl-methyl)-9H-fluorene 

Downstream Products

• 144772-00-9 [((phenyl)2C(C₅H₄)(fluorenyl^(1-)))Zr(methyl)2] 
• 460325-45-5 (C₆H₅)2C(C₅H₄)(C₁₃H₈)ZrCl(C₄H₉) 
• 920298-61-9 Ph₂C(cyclopentadienyl)(fluorenyl)ZrClMe 

Relevant articles and documents

Propylene polymerization of ansa-complexes (RXPh) 2C(Cp)(Flu)MCl2 (M = Zr or Hf) with halogen substituents on phenyl groups

The catalytic properties of (RXPh)2C(Cp)(Flu)MCl 2 complexes (RX = Cl, F or CF3; M = Zr or Hf) in propylene polymerization were studied. The results showed dependences of stereospecificity and polymer