Bis(cyclopentadienyl)dimethylzirconium

Base Information

• Chemical Name: Bis(cyclopentadienyl)dimethylzirconium
• CAS No.: 12636-72-5
• Molecular Formula: C12H16 Zr
• Molecular Weight: 251.483
• Hs Code.: 29310099
• European Community (EC) Number: 681-198-1
• Mol file: 12636-72-5.mol

Synonyms:BIS(CYCLOPENTADIENYL)DIMETHYLZIRCONIUM;zr(cp)2(me)2;Dimethyldicyclopentadienylzirconium;MFCD01073786;Bis(cyclopentadienyl)dimethylzirconium(IV), 97%

Chemical Property of Bis(cyclopentadienyl)dimethylzirconium

Chemical Property:

• Appearance/Colour: pale yellow to yellow crystals or needles
• Melting Point: 160-170 ºC
• Boiling Point: 170°C
• PSA: 0.00000
• LogP: 3.21060
• Storage Temp.: below 5° C
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 250.029899
• Heavy Atom Count: 13
• Complexity: 14.4

Purity/Quality:

98% ^*data from raw suppliers

Bis(Cyclopentadienyl)Dimethylzirconium ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [CH3-].[CH3-].[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Zr+2]
• Uses: Catalyst for:Cationic ring-opening polymerization reactionsMarkovnikov-selective intermolecular hydrothiolation of terminal alkynesZiegler-Natta polymerizations of alkenesMethylalumination of heterosubstituted arylethynesPrecatalyst for intramolecular hydroamination/cyclisation of aminoallenes

Technology Process of Bis(cyclopentadienyl)dimethylzirconium

There total 16 articles about Bis(cyclopentadienyl)dimethylzirconium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

zirconocene dichloride (1291-32-3) + methylmagnesium bromide (75-16-1) → bis(cyclopentadienyl)dimethylzirconium(IV) (12636-72-5)

Guidance literature:

In 1,4-dioxane; diethyl ether; at 21°C; a side-arm flask equipped with a stir bar charged with (C5H5)2ZrCl2 and diethyl ether, added a soln. ((C2H5)2O) of CH3MgBr (2.5 equiv.) with stirring, stirred at room temp. for 45 min, added dioxane, stirred for 1 h; volatiles removed under reduced pressure, solid extd. with toluene, filtered through Celite-padded coarse frit, filtrate collected, toluene removed under reduced pressure, product triturated with pentane, volatiles removed under reduced pressure;

DOI:10.1016/j.jallcom.2007.03.138

Reference yield: 87.0%

zirconocene dichloride (1291-32-3) + methyllithium (917-54-4) → bis(cyclopentadienyl)dimethylzirconium(IV) (12636-72-5)

Guidance literature:

In diethyl ether; at -78 - 20 ℃; for 2.5h; Glovebox; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.inorgchem.9b02213

Reference yield: 82.0%

2-lithiofuran (2786-02-9) + zirconocene methyl chloride → bis(cyclopentadienyl)dimethylzirconium(IV) (12636-72-5) + bis(2-furyl)zirconocen + methyl(2-furyl)zirconocene (139167-68-3)

Guidance literature:

In diethyl ether; byproducts: LiCl; inert atm., Schlenk technique; soln. of Zr-complex in ether cooled (-78°C), dropwise addn. of Li-salt in ether, warmed (over 12 h to ambient temp. with stirring); evapn., extn. (CHCl3), filtration, evapn. (brownish solid), mixt. not further purified; elem. anal., IR;;

DOI:10.1021/om00040a040

upstream raw materials:

methyllithium

zirconocene dichloride

methylmagnesium bromide

methyl-d3-magnesium iodide

Downstream raw materials:

chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II)

hydridochlorotris(triphenylphosphine)ruthenium(II)

{Zr₂(C₅H₅)4(HCCC(CH₃)3)(CH₃CHCHC(CH₃)3)}⁽¹⁺⁾*B(C₆H₄F)4^(1-) = {Zr₂(C₅H₅)4(HCCC(CH₃)3)(CH₃CHCHC(CH₃)3)}(B(C₆H₄F)4)

{Zr₂(C₅H₅)4(CH₃)(CH₂C(C₆H₄CH₃)(CH₃))}⁽¹⁺⁾*B(C₆H₄F)4^(1-) = {Zr₂(C₅H₅)4(CH₃)(CH₂C(C₆H₄CH₃)(CH₃))}(B(C₆H₄F)4)

Refernces

• 1、 McQuillan, G. P.,McKean, D. C.,Torto, I.. "INFRARED SPECTRA AND METHYL GROUP PROPERTIES IN DICYCLOPENTADIENYLDIMETHYL-TITATIUM(IV), -ZIRCONIUM(IV) AND -HAFNIUM(IV)". . p. 183 - 196. Retrieved 1986.
• 2、 Westmeier, Johannes,Pfaff, Christopher,Siewert, Juergen,Von Zezschwitz, Paultheo. "First tandem asymmetric conjugate addition of alkenyl nucleophiles and silyl trapping of the intermediate enolates". . p. 2651 - 2658. Retrieved 2013.
• 3、 Hupf, Emanuel,Tsuchiya, Yuki,Moffat, Wayne,Xu, Letian,Hirai, Masato,Zhou, Yuqiao,Ferguson, Michael J.,McDonald, Robert,Murai, Toshiaki,He, Gang,Rivard, Eric. "A Modular Approach to Phosphorescent π-Extended Heteroacenes". . p. 13323 - 13336. Retrieved 2019.
• 4、 Jordan, Richard F.. "LIGAND REDISTRIBUTION REACTIONS OF DICYCLOPENTADIENYLZIRCONIUM(IV) COMPLEXES". . p. 321 - 326. Retrieved 1985.
• 5、 Schmuck, Stefanie,Erker, Gerhard,Kotila, Sirpa. "C1-insertion reactions at cyclodimeric (η2-acetaldehyde)zirconocene complexes". . p. 75 - 86. Retrieved 1995.
• 6、 Vatamanu, Mihaela. "Observation of zirconium allyl species formed during zirconocene-catalyzed propene polymerization and mechanistic insights". . p. 112 - 120. Retrieved 2015/09/28.