134695-74-2

Basic information

• Product Name: TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE
• Synonyms: TMCP-TMS;TRIMETHYL(1,2,3,4-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE;TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE;2,3,4,5-TETRAMETHYLCYCLOPENTADIEN-1-3-YLTRIMETHYLSILANE;Tetramethylcyclopentadienyltrimethylsilane;(2,3,4,5-Tetramethyl-2,4-cyclopentadiene-1-yl)-trimethylsilane;2,3,4,5-TETRAMETHYLCYCLOPENTADIENYLTRIMETHYLSILANE;Trimethyl(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)silane
• CAS NO: 134695-74-2
• Molecular Formula: C₁₂H₂₂Si
• Molecular Weight: 194.39
• Product Categories: Alkenes;Cyclic;Organic Building Blocks
• Mol File: 134695-74-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 45°C 0,03mm
• Flash Point: 73°C
• Appearance: /
• Density: 0,852 g/cm3
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: 1.4860
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE(134695-74-2)
• EPA Substance Registry System: TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE(134695-74-2)

Safety Data

• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 134695-74-2(Hazardous Substances Data)

Usage

Description

TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE is a complex organic compound with the chemical formula C15H26Si. It is characterized by its unique structure, which includes a cyclopentadienyl ring with four methyl groups and a trimethylsilyl group attached to it. TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE is known for its potential applications in various chemical synthesis processes.

Uses

Used in Pharmaceutical Industry:
TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE is used as a synthetic intermediate for the production of aryl/heteroarylpiperazine derivatives. These derivatives are important in the development of various pharmaceutical compounds, particularly those with potential applications in the treatment of central nervous system disorders, such as schizophrenia and anxiety.
Used in Chemical Synthesis:
In the field of chemical synthesis, TRIMETHYL(2,3,4,5-TETRAMETHYL-2,4-CYCLOPENTADIEN-1-YL)SILANE serves as a versatile building block for the creation of more complex molecules. Its unique structure allows for a wide range of reactions, making it a valuable tool in the synthesis of various organic compounds, including those with potential applications in materials science, agrochemistry, and other specialized industries.

InChI:InChI=1/C12H22Si/c1-8-9(2)11(4)12(10(8)3)13(5,6)7/h12H,1-7H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 4249-10-9 1,2,3,4-tetramethylcyclopenta-1,3-diene 
• 82061-20-9 2,3,4,5-tetramethylcyclopent-2-en-1-ol 
• 54458-61-6 2,3,4,5-tetramethyl-2-cyclopenten-1-one 

Downstream Products

• 1228424-67-6 [(η5-(C5Me4SiMe3)(2-((N-2-methoxyphenyl)iminomethyl)pyrrole(1-))]Y(CH2SiMe3) 
• 304016-43-1 (tetramethylcyclopentadienyl)zirconium trichloride 

Relevant articles and documents

On the regioselectivity of alkylation of the (trimethylsilyl) tetramethylcyclopentadienide anion. A new approach to the synthesis of 1,2,3,4-tetramethylfulvene

The regioselectivity of alkylation of lithium (trimethylsilyl) tetramethylcyclopentadienide C5Me4SiMe3 -Li+ was studied by 1H and 13C NMR spectroscopy using its reactions with MeI, MeOTs, ClCH2CH 2Br, and ClCH2CH2I in different solvents as representative examples. Sterically non-hindered MeI and MeOTs presumably attack the C atom bonded to the silyl group giving 1,2,3,4,5- pentamethylcyclopentadienylsilane. For bulkier alkyl halides, such as ClCH 2CH2Br and ClCH2CH2I, the regioselectivity of alkylation changes to form preferentially gem-dialkyl-substituted cyclopentadienes. The reaction of C5Me 4SiMe3 -Li+ with formaldehyde affords 1,2,3,4-tetramethylfulvene in a high yield, providing an alternative synthetic approach to a number of ω-functionalized peralkylated cyclopentadienes. The quantum-chemical calculations of the C5Me 4SiMe3 - anion by the RHF and DFT (RMPW1PW91) methods in the valence-split 6-311+G(d,p) basis set are in good agreement with the experimental data.

Structural analysis of zincocenes with substituted cyclopentadienyl rings

New zincocenes [ZnCp′2] (2-5) with substituted cyclopentadienyl ligands C5Me4H, C5Me 4tBu, C5Me4SiMe2tBu and C 5Me4SiMe3, respectively, have been prepared by the reaction of ZnCl2 with the appropriate Cp′-transfer reagent. For a comparative structural study, the known [Zn(C5H 4SiMe3)2] (1), has also been investigated, along with the mixed-ring zincocenes [Zn(C5Me5)(C 5Me4SiMe3)] (6) and [Zn(C5Me 5)(C5H4SiMe3)] (7), the last two obtained by conproportionation of [Zn(C5Me5),] with 5 or 1, as appropriate. All new compounds were characterised by NMR spectroscopy, and by X-ray methods, with the exception of 7, which yields a side-product (C) upon attempted crystallisation. Compounds 5 and 6 were also investigated by 13C CPMAS NMR spectroscopy. Zincocenes 1 and 2 have infinite chain structures with bridging Cp′ ligands, while 3 and 4 exhibit slipped-sandwich geometries. Compounds 5 and 6 have rigid, η5/ η1(σ) structures, in which the monohapto C 5Me4SiMe3 ligand is bound to zinc through the silyl-bearing carbon atom, forming a Zn-C bond of comparable strength to the Zn-Me bond in ZnMe2. Zincocene 5 has dynamic behaviour in solution, but a rigid η5/η1(σ) structure in the solid state, as revealed by 13C CPMAS NMR studies, whereas for 6 the different nature of the Cp′ ligands and of the ring substituents of the η1-Cp′ group (Me and SiMe3) have permitted observation for the first time of the rigid η5/η1 solution structure. Iminoacyl compounds of composition [Zn(η5- C5Me4R)(η1-C(NXyl)C5Me 4R)] resulting from the reactions of some of the above zincocenes and CNXyl (Xyl = 2,6-dimethylphenylisocyanide) have also been obtained and characterised.

Influence electronique et sterique du ligand tetramethylcyclopentadienyle sur les proprietes physiques et sur la reactivite de complexes du titane et du zirconium

The complexes (C5Me4H)2MR1R2 (M=Ti, Zr) and (C5Me4H)(C5H5)MR1R2 (M=Ti) have been prepared (R1=R2=Cl, CH3, C6H5, p-C6H4CH3, CO; R1=Cl, R2=CH3, C6H5, p-C6H4CH3).The NMR and IR spectra of these complexes indicate that C5Me4H exhibits an electron-donor effect more important than C5H5 and a little bit weaker than that of C5Me5.A structural investigation of the complex (C5Me4H)2Zr(C6H5)Cl and the study of the 1H or 13C dynamic NMR properties of the compounds (C5Me4H)2MR1R2 (M=Ti, Zr; R1=R2=C6H5, p-C6H4CH3; R1=Cl, Br, R2=C6H5, p-C6H4CH3) show clearly that C5Me4H has a steric effect intermediate between C5H5 and C5Me5.The steric or electronic effects of C5Me4H have been used to induce specific isomerization reactions of various alkenes by using (C5Me4H)2Ti(CH3)2 as catalyst. --- Key words: zirconium, titanium, tetramethylcyclopentadienyl, photo-assisted, isomerization.