1068-69-5

Basic information

• Product Name: TRIS(TRIMETHYLSILYL)METHANE
• Synonyms: TRIS(TRIMETHYLSILYL)METHANE 97+%;Tris(trimethylsilyl)methane,min.97%;Tris(trimethylsilyl)methane, min. 97%;2,2,4,4-Tetramethyl-3-(trimethylsilyl)-2,4-disilapentane;Methanetriyltris(trimethylsilane);Methylidynetris(trimethylsilane);Tris(trimethylsilyl)methane,93%;1,1',1''-Methylidynetris[1,1,1-trimethylsilane]
• CAS NO: 1068-69-5
• Molecular Formula: C₁₀H₂₈Si₃
• Molecular Weight: 232.59
• Product Categories: Organometallic Reagents;Organosilicon;Others;organosilicon compounds
• Mol File: 1068-69-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 55-56 °C2 mm Hg(lit.)
• Flash Point: 170 °F
• Appearance: colorless/liquid
• Density: 0.827 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0467mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Solubility: sol common organic solvents.
• BRN: 1850371
• CAS DataBase Reference: TRIS(TRIMETHYLSILYL)METHANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(TRIMETHYLSILYL)METHANE(1068-69-5)
• EPA Substance Registry System: TRIS(TRIMETHYLSILYL)METHANE(1068-69-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 1068-69-5(Hazardous Substances Data)

Usage

Description

Tris(trimethylsilyl)methane, also known as trisylmethane, is a sterically demanding and versatile organic compound with the molecular formula (Me3Si)3CH. It features a central carbon atom bonded to three trimethylsilyl groups, which impart unique steric and electronic properties to the molecule. Tris(trimethylsilyl)methane is a clear, colorless liquid with a boiling point of 219°C and a density of 0.836 g/cm3. Its refractive index is 1.4657, and it is used as a precursor in various chemical reactions and applications.

Uses

Used in Organic Synthesis:
Tris(trimethylsilyl)methane is used as a precursor for (Me3Si)3CLi, which is useful for introducing the bulky tris(trimethylsilyl)methyl (trisyl) group into organic molecules. This group can improve the stability and reactivity of certain compounds, making it a valuable tool in organic synthesis.
Used in Peterson Alkenation:
Tris(trimethylsilyl)methane serves as a reagent in the Peterson alkenation reaction, a widely used method for the synthesis of alkenes. The trisyl group can be selectively removed under mild conditions, allowing for the formation of the desired alkene product.
Used in Synthesis of Tris(trimethylsilyl)methyl Bromide:
Tris(trimethylsilyl)methane is used in the synthesis of tris(trimethylsilyl)methyl bromide, a valuable intermediate in organic chemistry. Tris(trimethylsilyl)methane can be further transformed into other useful reagents and building blocks.
Used in Metalation Reactions:
The tris(trimethylsilyl)methyl group can be deprotonated to form bis(trimethylsilyl)methyllithium, which can act as a nucleophile in various metalation reactions. This allows for the formation of new chemical bonds and the synthesis of complex organic molecules.
Used in Hydrosilylation of Double Bonds:
Tris(trimethylsilyl)methane can participate in hydrosilylation reactions, where a silicon-hydrogen bond is added across a carbon-carbon double bond. This reaction is useful for the synthesis of various organosilicon compounds and can improve the stability and reactivity of certain molecules.
Used in Intramolecular Reactions:
The sterically demanding nature of tris(trimethylsilyl)methane allows it to participate in intramolecular reactions, where the trisyl group can react with another part of the same molecule. This can lead to the formation of cyclic compounds and other complex structures.
Used in Intermolecular Reactions:
Tris(trimethylsilyl)methane can also be involved in intermolecular reactions, where the trisyl group reacts with a different molecule. This can lead to the formation of new compounds and the creation of novel chemical entities.
Used in Nonradical Reactions:
The tris(trimethylsilyl)methyl group can participate in nonradical reactions, where it can be selectively introduced and removed without the formation of radicals. This can be advantageous in certain synthetic routes, as it allows for greater control over the reaction conditions and product formation.

InChI:InChI=1/C10H28Si3/c1-11(2,3)10(12(4,5)6)13(7,8)9/h10H,1-9H3

Upstream product

• 56-23-5 tetrachloromethane 
• 75-77-4 chloro-trimethyl-silane 
• 67-66-3 chloroform 
• 75-25-2 Bromoform 
• 15951-41-4 bis(trimethylsilyl)dichloromethane 

Downstream Products

• 5654-07-9 1,1-bis(trimethylsilyl)ethylene 
• 51318-07-1 1,1-diphenyl-2-trimethylsilylethene 
• 51318-08-2 ((Z)-3,3-Dimethyl-2-phenyl-but-1-enyl)-trimethyl-silane 
• 72190-77-3 [Chloro-(tris-trimethylsilanyl-methyl)-silanyl]-benzene 
• 72190-82-0 [Methyl-(tris-trimethylsilanyl-methyl)-silanyl]-benzene 
• 72190-81-9 [Fluoro-methyl-(tris-trimethylsilanyl-methyl)-silanyl]-benzene 
• 68260-14-0 (diphenyl)fluorosilane 
• 72190-80-8 [Methoxy-methyl-(tris-trimethylsilanyl-methyl)-silanyl]-benzene 
• 72208-75-4 C₂₃H₄₀OSi₄ 
• 18415-23-1 1,1-bis(trimethylsilyl)-2-phenylethylene 
• 26608-69-5 2-(tert-butyl)-1,1-bis(trimethylsilyl)ethylene 
• 72190-66-0 [Dichloro-(tris-trimethylsilanyl-methyl)-silanyl]-benzene 
• 62762-16-7 4-Phenyl-1,1-bis(trimethylsilyl)-1,3-butadien 
• 72190-75-1 C₂₂H₃₇ClSi₄ 

Relevant articles and documents

Crystal structures of organometallic compounds of lithium and magnesium containing the bulky ligands C(SiMe3)2(SiMe2X) X=Me, Ph, NMe2, or C5H4N-2

The complex [Li(TMEDA){C(SiMe3)2SiMe2NMe2}] (1) (TMEDA=N,N,N′,N′-tetramethylethane-1,2,-diamine) was found to crystallise with an internally coordinated structure like that of [Li(THF)2{C(SiMe3)2SiMe2NMe 2}] (THF=tetrahydrfuran). In contrast, the compound with Ph in place of NMe2 crystallised as a dialkyllithate [Li(TMEDA)2][Li{C(SiMe3)2(SiMe 2Ph)}2] (4). The reaction of 4 with MgBr2 gave the doubly bromide-bridged lithium-magnesium complex [Li(TMEDA)(μ-Br)2Mg{C(SiMe3)2(SiMe 2Ph)}(THF)] (6), and that of [Li(THF){C(SiMe3)2(SiMe2C5H 4N-2)}] gave the singly bridged compound [Li(THF)3(μ-Br)MgBr{C(SiMe3)2(SiMe 2C5H4N-2)] (8). The Grignard reagents [Mg{C(SiMe3)3}I(OEt2)]2 (10) and [Mg{C(SiMe3)2 (SiMe2Ph)}I(OEt2)]2 (11) were obtained from the reactions between (Me3Si)3CI and (Me2Ph)(Me3Si)CI, respectively, with magnesium metal and shown to have halide-bridged structures. The unsymmetrical dialkylmagnesium [MgBu{C(SiMe3)2(SiMe2NMe2)}(THF)] (13), was prepared from a mixture of LiBu, 1 and [MgBr2 (OEt2)2].

Properties of Chalcogen-Chalcogen Bonds, XVII. - Di- and Trisulfanes with Sterically Congested Alkyl Substtuents: The First trans-Dialkyldisulfane

Bistrisulfane (1) is obtained from tris(trimethylsilyl)methyllithium and sulfur with subsequent oxidation by oxygen or from tris(trimethylsilyl)methanethiol with sulfur dichloride.The solid trisulfane contains a transoid (helical) C-S-S-S-C backbone without severe distortion from steric strain.Desulfuration of the byproduct bistetrasulfane (2) with mercury provides 1, but further desulfuration of 1 to bisdisulfane (3) has not been achieved. 3 was isolated after oxidation of lithium tris(trimethylsilyl)methanethiolate with bromine. 3 contains a trans-C-S-S-C moiety with an unusually long S-S bond (210-211 pm).The less crowded bis(triphenylmethyl)disulfane (4) contains a "normal" C-S-S-C moiety with anticlinal conformation (torsion angle -110 deg). Key Words: Disulfanes / Trisulfanes / Bond conformations, S-S

ZUR HERSTELLUNG UND REAKTIVITAET VON BIS(TRIMETHYLSILYL)DILITHIOMETHAN

At -90 deg C in THF or similar media bis(trimethylsilyl)dichloromethane 2 reacts with lithium-4,4'-di-tert-butylbiphenyl (LiDBB) or suspensions of freshly sublimed lithium to give the title compound 1 that can bind two equivalents of various electrophiles. 1 has a great propensity for proton abstraction and it is markedly less reactive towards ethyl iodide than (Me3Si)2EtCLi 6.