125542-03-2

Basic information

• Product Name: CHLORODIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE
• Synonyms: CHLORODIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE;chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopenta;ChlorodiMethyl(2,3,4,5-tetraMethyl-2,4-cyclopentadien-1-yl)silane 97%
• CAS NO: 125542-03-2
• Molecular Formula: C₁₁H₁₉ClSi
• Molecular Weight: 214.81
• Product Categories: Protecting and Derivatizing Reagents;Protection and Derivatization;Silicon-Based
• Mol File: 125542-03-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 50 °C0.05 mm Hg(lit.)
• Flash Point: 133 °F
• Appearance: /
• Density: 0.972 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.125mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• CAS DataBase Reference: CHLORODIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLORODIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE(125542-03-2)
• EPA Substance Registry System: CHLORODIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE(125542-03-2)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 2986 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 125542-03-2(Hazardous Substances Data)

Usage

General Description

Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)Silane is a chemical compound with a complex structure. It is known for its organometallic nature, meaning it contains a metal-carbon bond, in this case involving silicon. The molecule is characterized by the presence of a silicon atom, a chloro group, two methyl groups, and an attached cyclic compound - a 2,4-cyclopentadiene ring with four additional methyl groups. It is possible that this compound could act as a reagent for various chemical reactions or serve as an intermediate in the synthesis of other complex organic compounds, but specific applications would depend on its reactivity and stability under the conditions of interest.

InChI:InChI=1/C11H19ClSi/c1-7-8(2)10(4)11(9(7)3)13(5,6)12/h11H,1-6H3

Synthetic route

lithium 1,2,3,4-tetramethylcyclopentadienide (386708-10-7, 82061-21-0) + dimethylsilicon dichloride (75-78-5) → 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2)

Conditions	Yield
In tetrahydrofuran at -30 - 20℃; Inert atmosphere;	88%

1,2,3,4-tetramethylcyclopenta-1,3-diene (4249-10-9) + dimethylsilicon dichloride (75-78-5) → 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2)

Conditions	Yield
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In diethyl ether; hexane Stage #2: dimethylsilicon dichloride In tetrahydrofuran	83%
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In tetrahydrofuran at -78 - 20℃; Schlenk technique; Stage #2: dimethylsilicon dichloride In tetrahydrofuran; hexane at 20℃; Schlenk technique;	83%
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In tetrahydrofuran at -78 - 20℃; Schlenk technique; Stage #2: dimethylsilicon dichloride In tetrahydrofuran; hexane at -78 - 20℃; Schlenk technique;	83%

dimethylsilicon dichloride (75-78-5) + 2,3,4,5-tetramethylcyclopentadienyl sodium → 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2)

Conditions	Yield
In tetrahydrofuran for 16h;

2,3,4,5-tetramethyl-2-cyclopenten-1-one (54458-61-6) → 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium aluminium hydride / diethyl ether / 2 h 1.2: 37 percent / hydrochloric acid; air / diethyl ether; H2O / 16 h 2.1: n-butyllithium / petroleum ether / 16 h / 0 - 20 °C 2.2: 67 percent / petroleum ether; tetrahydrofuran / 16 h View Scheme

C11H15(1-)*Li(1+) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C22H34Si

Conditions	Yield
In tetrahydrofuran at -25 - 20℃; Inert atmosphere; Glovebox;	98.9%

Li(1+)*C5H4C(CH3)2CH2CH2CHCH2(1-)=LiC5H4C(CH3)2CH2CH2CHCH2 + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C23H36Si

Conditions	Yield
In tetrahydrofuran at 20℃; for 6h;	98%

1,3-diisopropyl-4,5-dimethyl-1H-imidazol-2(3H)-imine + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C5(CH3)4HSi(CH3)2NCN2(CH(CH3)2)2C2(CH3)2 (1034125-20-6)

Conditions	Yield
In hexane at 20℃; for 1.5h;	98%

1-n-butyl-3H-indene (2294-88-4) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C24H34Si

Conditions	Yield
Stage #1: 1-n-butyl-3H-indene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2.5h; Schlenk technique; Stage #2: 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene In tetrahydrofuran at -78 - 20℃; Schlenk technique;	98%

2-thiazolylamine (96-50-4) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → (C5Me4H)SiMe2NH-2-thiazole (1000392-78-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 3h;	97%

1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) + K(1+)*C5H4CH2CH2P(C6H5)2(1-)=K[C5H4CH2CH2P(C6H5)2] → (2-{4-[dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-cyclopenta-1,3-dienyl}-ethyl)-diphenyl-phosphane

Conditions	Yield
In tetrahydrofuran at 20℃; for 18h;	96%

1,4-diisopropyl-1,4,7-triazacyclononane lithium + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → 1-[dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-4,7-diisopropyl-[1,4,7]triazonane (325791-08-0)

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	96%

lithium 2,4,6-trimethylaniline (65768-38-9) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → (CH3)2Si(C5(CH3)4H)NHC6H2(CH3)3 (500906-70-7)

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	96%

C15H19(1-)*Li(1+) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C26H36Si(2-)*2H(1+)

Conditions	Yield
In tetrahydrofuran at -100 - 20℃; Inert atmosphere;	96%

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → [2-(2-Methoxy-ethoxy)-ethoxy]-dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silane (142992-74-3)

Conditions	Yield
With pyridine In diethyl ether Ambient temperature;	95%

pyrrolidine (123-75-1) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C15H27NSi (1450982-86-1)

Conditions	Yield
Stage #1: pyrrolidine With n-butyllithium In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	95%

4-(4-(tert-butyl)phenyl)-2-methyl-1H-indene + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → dimethyltetramethylcyclopentadienyl-2-methyl-4-(4-tert-butylphenyl)indenyl silane

Conditions	Yield
Stage #1: 4-(4-(tert-butyl)phenyl)-2-methyl-1H-indene With n-butyllithium In tetrahydrofuran; hexane; toluene at -10 - 20℃; for 12h; Stage #2: 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene In tetrahydrofuran; hexane; toluene at -10 - 20℃; for 12h;	95%

1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) + lithium (diphenylphosphino)cyclopentadienide → {4-[dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-cyclopenta-1,3-dienyl}-diphenyl-phosphane

Conditions	Yield
In tetrahydrofuran at 20℃; for 18h;	94%

1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) + 2-phenyl-2-propylamine (585-32-0) → C5Me4HSiMe2N(H)CMe2Ph (1290103-43-3)

Conditions	Yield
Stage #1: 2-phenyl-2-propylamine With n-butyllithium In tetrahydrofuran Inert atmosphere; Stage #2: 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene In tetrahydrofuran at -78℃; Inert atmosphere;	94%

2,5-dimethylpyrrolyl lithium salt + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C17H27NSi

Conditions	Yield
In tetrahydrofuran for 24h; Schlenk technique; Glovebox; Inert atmosphere;	93%

Li{C5H4(CMe2CH2CH2CH=CMe2)} + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C25H40Si (1187773-75-6)

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	92%

2-[2-(1H-inden-1-yl)ethyl]-1,3-dioxane (1139269-81-0) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C26H36O2Si (1139269-88-7)

Conditions	Yield
With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 20.25h; Inert atmosphere; Schlenk technique;	91%
Stage #1: 2-[2-(1H-inden-1-yl)ethyl]-1,3-dioxane With n-butyllithium In diethyl ether; hexane at 20℃; for 4h; Stage #2: 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene In diethyl ether; hexane at 20℃; for 15h; Further stages.;	60%

tert.-butyl lithium (594-19-4) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → [C5(CH3)4(Si(CH3)2C(CH3)3)](1-)*Li(1+)=[C5(CH3)4(Si(CH3)2C(CH3)3)Li]

Conditions	Yield
In tetrahydrofuran; pentane 1.) -78 deg C, 1 h, 2.) r.t., 2 h;	90%

n-butyllithium (109-72-8, 29786-93-4) + 1,2-dicarba-closo-dodecaborane(12) (16872-09-6) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → Me2Si(C5Me4H)(o-carboranyl) (318955-29-2)

Conditions

Yield

With NH4Cl In diethyl ether; hexane; benzene 2 equiv. of n-BuLi in hexane was added to soln. of o-carborane in C6H6/Et2O (2:1) at 0 °C under N2, mixt. was warmed to room temp. and stirred for 2 h, Si-compd. was added, mixt. was refluxed overnight, satd. aq. soln. of NH4Cl was added; aq. layer was extd. with Et2O, ext. was combined with org. layer and dried over MgSO4, soln. was filtered, solvent was removed, residue was chromd. on silica with n-hexane;

90%

1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) + C5H7K*C4H8O → Dimethyl-((E)-penta-2,4-dienyl)-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silane

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	88%

C15H18BN2(1-)*Li(1+) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → 6-(2-(diethylboryl)phenyl)-N-(dimethylsilyl-(2,3,4,5-tetramethylcyclopenta-2,4-dienyl))pyridin-2-amine

Conditions	Yield
Stage #1: C15H18BN2(1-)*Li(1+); 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene In tetrahydrofuran at -30 - 20℃; Inert atmosphere; Stage #2: In tetrahydrofuran at -30 - 20℃;	88%

1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) + C18H15NP(1-)*Li(1+) → [dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-(2-diphenylphosphanyl-phenyl)-amine

Conditions	Yield
In hexane at 20℃; for 14h; Alkylation;	86%

triethylene glucol monomethyl ether (112-35-6) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → {2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silane (142992-76-5)

Conditions	Yield
With pyridine In diethyl ether Ambient temperature;	85%

lithium benzylamide (38225-27-3) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → Benzyl-[dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-amine

Conditions	Yield
In hexane 1) -78 deg C, 2) r.t., 14 h;	84%

2-aminopyridine (504-29-0) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → (C5Me4H)SiMe2NH-2-pyridine (231304-97-5)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 3h;	84%

3-biphenyl amine (2243-47-2) + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → N-(biphenyl-3-yl)-1,1-dimethyl-1-(2,3,4,5-tetramethylcyclopenta-2,4-dienyl)silylamine (1292186-51-6)

Conditions	Yield
Stage #1: 3-biphenyl amine With n-butyllithium In diethyl ether; hexane at -40 - 20℃; for 1h; Inert atmosphere; Stage #2: 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene In diethyl ether; hexane at -40 - 20℃; for 8h;	84%

1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) + (N,N-dimethylaminoethyl)cyclopentadienyl sodium → (2-{3-[Dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-cyclopenta-1,4-dienyl}-ethyl)-dimethyl-amine

Conditions	Yield
In tetrahydrofuran for 12h;	83%

C17H16O + 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene (125542-03-2) → C28H34OSi

Conditions	Yield
Stage #1: C17H16O With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene With 1,3-dimethyl-2-imidazolidinone In tetrahydrofuran; hexane at -20 - 20℃; for 16h; Inert atmosphere;	83%

Upstream product

• 10060-55-6 (2,3,4,5-tetramethyl)cyclopentadiene 
• 75-78-5 dimethylsilicon dichloride 
• 386708-10-7 lithium 1,2,3,4-tetramethylcyclopentadienide 
• 54458-61-6 2,3,4,5-tetramethyl-2-cyclopenten-1-one 
• 4249-10-9 1,2,3,4-tetramethylcyclopenta-1,3-diene 

Downstream Products

• 1292186-51-6 N-(biphenyl-3-yl)-1,1-dimethyl-1-(2,3,4,5-tetramethylcyclopenta-2,4-dienyl)silylamine 
• 324029-08-5 N-[dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-N'-phenyl-benzene-1,2-diamine 
• 185432-70-6 [Dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-((R)-1-phenyl-ethyl)-amine 
• 134849-05-1 Dimethyl-phenoxy-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silane 
• 134849-06-2 1,3-Bis-[dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyloxy]-benzene 
• 134849-08-4 1,3,5-Tris-[dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyloxy]-benzene 

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METALLOCENE COMPOUND AND CATALYST FOR POLYMERIZATION OF POLYOLEFIN COMPRISING SAME

The present invention provides a metallocene compound that can be firmly supported on a carrier by improving binding force with the carrier, and a catalyst for polymerization of polyolefin comprising the metallocene compound. According to the present invention, provided is the metallocene compound into which a silane group is introduced.

Metallocene compound, catalyst component for olefin polymerization and catalyst for olefin polymerization containing the same, and method for producing olefin polymer using catalyst for olefin polymerization

The metallocene compound represented by the following general formula (1): (the numerals and signs in the general formula (1) are as described in the description).

POLYOLEFIN CATALYST AND PREPARING METHOD OF POLYOLEFIN USING SAME

The present invention discloses a novel metallocene catalyst and a method for manufacturing a polyolefin having a high molecular weight and a low melt index using the same. The novel metallocene catalyst of the present invention has excellent activity relative to existing catalysts and enables the production of the polyolefin having the high molecular weight and the low melt index.COPYRIGHT KIPO 2019