73364-10-0

Basic information

• Product Name: Bis(n-butylcyclopentadienyl)zirconium dichloride
• Synonyms: bis(n-butylcyclopentadienyl)zirkoniumdichloride;bis[(1,2,3,4,5-.eta.)-1-butyl-2,4-cyclopentadien-1-yl]dichloro-zirconiu;1,1'-DIBUTYLZIRCONOCENE DICHLORIDE;BIS(BUTYLCYCLOPENTADIENYL)ZIRCONIUM DICHLORIDE;BIS(BUTYLCYCLOPENTADIENYL)ZIRCONIUM(IV) DICHLORIDE;BIS-(BUTYLCYCLOPENTADIENYL)-DICHLOROZIRCONIUM(IV);BIS(N-BUTYLCYCLOPENTADIENYL)ZIRCONIUM DICHLORIDE;BIS(N-BUTYLCYCLOPENTADIENYL)ZIRCONIUM(IV) DICHLORIDE
• CAS NO: 73364-10-0
• Molecular Formula: C₁₈H₂₆Cl₂Zr
• Molecular Weight: 404.53
• EINECS: 416-980-1
• Product Categories: Classes of Metal Compounds;Metallocenes;Titanocene, etc.;Transition Metal Compounds;Zr (Zirconium) Compounds;Catalysis and Inorganic Chemistry;Chemical Synthesis;Zirconium;metallocene
• Mol File: 73364-10-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 98.7-99.4 °C(lit.)
• Appearance: off-white/Powder
• Sensitive: Air & Light Sensitive
• CAS DataBase Reference: Bis(n-butylcyclopentadienyl)zirconium dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(n-butylcyclopentadienyl)zirconium dichloride(73364-10-0)
• EPA Substance Registry System: Bis(n-butylcyclopentadienyl)zirconium dichloride(73364-10-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26-24/25
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 73364-10-0(Hazardous Substances Data)

Usage

Chemical Properties

Bis(n-butylcyclopentadienyl)zirconium dichloride is a white crystalline powder or needles.

Uses

Catalyst for:Copolymerization of ethylene-alpha-olefinEthylene polymerizationMetallocene supported catalyst

InChI:InChI=1/2C9H13.2ClH.Zr/c2*1-2-3-6-9-7-4-5-8-9;;;/h2*4-5,7-8H,2-3,6H2,1H3;2*1H;/q;;;;+2/p-2/r2C9H13.Cl2Zr/c2*1-2-3-6-9-7-4-5-8-9;1-3-2/h2*4-5,7-8H,2-3,6H2,1H3;

Synthetic route

n-butyl cyclopentadiene (62247-87-4) + 1-(n-C4H9)C5H5 (78347-54-3) + zirconium(IV) chloride (10026-11-6) → bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; 1,2-dimethoxyethane; hexane 1:1 mixt. of 1- and 2-(n-C4H9)C5H5 was dissolved in THF and treated with n-BuLi in hexane followed by ZrCl4 in glyme; recrystd. from heptane; elem. anal.;	68%

lithium aluminium tetrahydride (16853-85-3) + bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0) → (n-BuCp)2ZrH3AlH2 (914809-03-3)

Conditions	Yield
In diethyl ether (inert atmosphere); a soln. of Zr complex stirred at 0°C, LiAlH4 in Et2O added, allowed to warm to room temp.; filtered, evapd.;	99%
In diethyl ether byproducts: LiCl; suspn. of (nBuCp)2ZrCl2 (3.2 mmol) in ether prepared in Schlenk flask under Ar; soln. of LiAlH4 (7.07 mmol) in ether added (0°C); kept (30 min, 0°C); filtered; concd. to dryness (vac.); extd. into toluene; filtered; concd.to dryness (vac.);

bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0) + zirconium(IV) chloride (10026-11-6) → (n-butylcyclopentadienyl)zirconium chloride

Conditions	Yield
In toluene at 120℃; for 16h; Schlenk technique;	99%

bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0) + zirconium(IV) chloride (10026-11-6) → (2-butylcyclopenta-2,4-dienyl)zirconium(IV) chloride (329735-75-3)

Conditions	Yield
In toluene at 20℃; for 20h; Heating / reflux;	87%

bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0) + silver(I) perfluorooctane sulfonate (3824-94-0) + water (7732-18-5) → [n-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4*6H2O

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Darkness; Inert atmosphere;	65%

bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0) + hex-3-yne (928-49-4) → 2-n-butyl-4,5,6,7-tetraethylindene (1160580-39-1)

Conditions	Yield
Stage #1: bis(n-butylcyclopentadienyl)zirconium dichloride With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: hex-3-yne In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With titanium tetrachloride In tetrahydrofuran; hexane at 20℃; for 3h;	17%

bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0) + trideuteriomethyl-lithium (15772-82-4) → (C4H9C5H4)2Zr(CD3)2

Conditions	Yield
In diethyl ether according to Samuel, E.; Rausch, M.D. J.Am. Chem. Soc. 1973, 96, 6263; quenched by Me3SiCl, isolated by extn. wiht hexane, purity was verified by NMR and mass spectroscopy;

bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0) + trimethylaluminum (75-24-1) → (Cp-n-Bu)2ZrClMe (107810-21-9)

Conditions	Yield
In (2)H8-toluene at 20°C; not isolated, detected by NMR;

bis(n-butylcyclopentadienyl)zirconium dichloride (73364-10-0) + trimethylaluminum (75-24-1) + trityl tetrakis(pentafluorophenyl)borate → [(Cp-n-Bu)2Zr(μ-Me)2AlMe2][B(C6F5)4]

Conditions	Yield
In (2)H8-toluene at 20°C; not isolated, detected by NMR;

Upstream product

• 62247-87-4 n-butyl cyclopentadiene 
• 78347-54-3 1-(n-C₄H₉)C₅H₅ 
• 10026-11-6 zirconium(IV) chloride 

Downstream Products

• 329735-75-3 (2-butylcyclopenta-2,4-dienyl)zirconium(IV) chloride 
• 511512-72-4 Me2Al(μ-OSiMe2C(CH3)3)2AlMeCl 
• 511512-80-4 [((n-C4H9)C5H4)2ZrCl(μ-Cl)ClZr((n-C4H9)C5H4)2][B(C6F5)4] 
• 511512-71-3 Me2Al(μ-OSi(OSiMe3)3)2AlMeCl 
• 1265631-38-6 [(n-BuC5H4)2Zr(μ-H)3(Al(i-Bu)2)2][B(C6F5)4] 
• 107810-21-9 (Cp-n-Bu)2ZrClMe 

Relevant articles and documents

NMR assignments of alkylcyclopentadienyl ligands in zirconium and platinum complexes

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