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

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

Uses

Used in Polymer Industry:
Bis(n-butylcyclopentadienyl)zirconium dichloride is used as a catalyst for the copolymerization of ethylene-alpha-olefin. It facilitates the formation of copolymers with improved properties, such as enhanced strength, flexibility, and resistance to environmental factors.
Used in Ethylene Polymerization:
In the ethylene polymerization process, Bis(n-butylcyclopentadienyl)zirconium dichloride acts as a metallocene-supported catalyst. It helps in the production of polyethylene with specific molecular weights, structures, and properties, which can be tailored for various applications.
Used in Catalyst Industry:
Bis(n-butylcyclopentadienyl)zirconium dichloride is used as a catalyst in various chemical reactions, including the synthesis of olefins, aromatics, and other hydrocarbons. Its unique structure and properties make it an efficient and selective catalyst, improving the yield and quality of the desired products.

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 
• 107810-21-9 (Cp-n-Bu)2ZrClMe 
• 1265631-38-6 [(n-BuC5H4)2Zr(μ-H)3(Al(i-Bu)2)2][B(C6F5)4]