Vinyltrimethylsilane

Base Information

• Chemical Name: Vinyltrimethylsilane
• CAS No.: 754-05-2
• Molecular Formula: C5H12Si
• Molecular Weight: 100.236
• Hs Code.: 29319090
• European Community (EC) Number: 212-042-9
• NSC Number: 93553
• UNII: H5HJ2RET1N
• DSSTox Substance ID: DTXSID1061071
• Nikkaji Number: J120.971J
• Wikipedia: Nysted_reagent
• Wikidata: Q72516420
• Mol file: 754-05-2.mol

Synonyms:Vinyltrimethylsilane;754-05-2;trimethyl(vinyl)silane;Ethenyltrimethylsilane;Trimethylvinylsilane;Silane, ethenyltrimethyl-;(Trimethylsilyl)ethylene;Silane, trimethylvinyl-;ethenyl(trimethyl)silane;H5HJ2RET1N;C5H12Si;EINECS 212-042-9;MFCD00008606;NSC 93553;NSC-93553;Vinyl trimethylsilane;Vinyltrimethysilane;NSC93553;trimethylsilyl ethene;(trimethylsilyl)ethene;vinyl trimethyl silane;41114-59-4;UNII-H5HJ2RET1N;Vinyltrimethylsilane, 97%;CH2=CHSi(CH3)3;TRIMIPRAMINEMALEATESALT;DTXSID1061071;Vinyltrimethylsilane, >=99.5%;AMY1250;AKOS015909455;GS-6896;PB48764;s22050;BP-21122;FT-0651758;V0067;W-139;EN300-111842;Trimethyl(vinyl)silane, purum, >=97.0% (GC);A851124;J-525108;(Trimethylsilyl)ethylene, Ethenyltrimethylsilane, Trimethyl(vinyl)silane

Chemical Property of Vinyltrimethylsilane

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 4.44 psi ( 20 °C)
• Melting Point: -132°C
• Refractive Index: n20/D 1.391(lit.)
• Boiling Point: 54.999 °C at 760 mmHg
• Flash Point: <-30 °C
• PSA: 0.00000
• Density: 0.706 g/cm³
• LogP: 2.04980
• Storage Temp.: Flammables area
• Solubility.: Miscible with tetrahydrofuran, diethyl ether, benzene and dichlo
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 100.070826917
• Heavy Atom Count: 6
• Complexity: 49.4

Purity/Quality:

95% ^*data from raw suppliers

Vinyltrimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-22-36/37/38-40
• Safety Statements: 16-26-33-36-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: C[Si](C)(C)C=C
• General Description: Vinyltrimethylsilane is a key organosilane compound used in hydroboration reactions, where it serves as a substrate to study regiospecific transformations. The hydroboration of Vinyltrimethylsilane demonstrates high selectivity, with boron predominantly attaching to the terminal position of the double bond, leading to products with high isomeric purity. This reaction highlights the unique directive influence of the trimethylsilyl group and contributes to the synthesis of functionalized organosilanes, making it a valuable tool in synthetic organic chemistry.

Technology Process of Vinyltrimethylsilane

There total 77 articles about Vinyltrimethylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(CH3)3SiCHCH2(SFe(CO)3)2 + nitric acid (7697-37-2,78989-43-2) → ferric nitrate (7782-61-8) + ethenyltrimethylsilane (754-05-2)

Guidance literature:

In nitric acid; byproducts: H2SO4, NO, CO; stirring for 0.5 h at 25°C; condensing silane in a trap cooled with solid CO2, treating aq. layer with NaOH, evapn. to dryness, IR;

Reference yield: 96.0%

→ 3,8-bis(trimethylsilyl)-1,2,5,6-tetrathiacyclooctane (87495-58-7) + ethenyltrimethylsilane (754-05-2)

Guidance literature:

With copper dichloride; In benzene; at 80 ℃; for 8h;

Reference yield: 95.0%

chloro-trimethyl-silane (75-77-4) + Vinyl bromide (593-60-2,25951-54-6) → ethenyltrimethylsilane (754-05-2)

Guidance literature:

Vinyl bromide; With magnesium; In tetrahydrofuran; for 1h; Reflux;

chloro-trimethyl-silane; In tetrahydrofuran; Reflux;

upstream raw materials:

chloro-trimethyl-silane

chloroethylene

vinyl magnesium bromide

trichlorovinylsilane

Downstream raw materials:

6,6-dimethyl-3-thia-6-sila-heptanoic acid

(phenylethyl)silane

1-phenyl-3-trimethylsilanyl-propan-1-one

phenyl 2-(trimethylsilyl)ethyl sulfide

Refernces

Hydroboration. 56. Convenient and Regiospecific Route to Functionalized Organosilanes through the Hydroboration of Alkenylsilanes.

10.1021/jo01306a006

The research investigates the hydroboration of various alkenylsilanes to develop a systematic and detailed understanding of the products formed and the utility of this reaction for synthesizing functionalized organosilanes. The study aims to resolve long-standing anomalies in the hydroboration of alkenylsilanes and provide a clear understanding of the phenomena involved. Vinyltrimethylsilane (1) is a key substrate used to study the hydroboration reaction. Allyltrimethylsilane (24) is another important substrate used in the research to explore the hydroboration reaction and its outcomes. The research finds that the hydroboration process is highly regiospecific, with the boron atom predominantly placed at the terminal position of the double bond, resulting in high isomeric purity of the products. The study also observes unusual directive effects of the trimethylsilyl substituent and synthesizes the first monomeric dialkylborane without the need for excess alkene. The findings provide valuable insights into the hydroboration mechanism and offer a convenient route to functionalized organosilanes for use in synthetic organic chemistry.