754-05-2 Usage
Description
Vinyltrimethylsilane, also known as (triethylsilyl)acetylene, is an organosilicon compound with the chemical formula (CH3)3SiC2H3. It is a clear, colorless liquid with a boiling point of 55-57 °C and a density of 0.691 g/cm3 at 20°C. It is widely used in various chemical reactions and industries due to its unique properties and reactivity.
Uses
1. Used in Semiconductor Processing:
Vinyltrimethylsilane is used as a precursor in semiconductor processing, particularly in the preparation of silyl-ethers by Rh(I) catalysis. It plays a crucial role in the development of advanced semiconductor materials and devices.
2. Used in Organic Synthesis:
Vinyltrimethylsilane is used as an ethylene equivalent in electrophilic substitution reactions. It serves as a versatile building block for the synthesis of various organic compounds, including:
a. 3-Trimethylsilyl-3-buten-2-one, a methyl vinyl ketone surrogate for Robinson annulations.
b. α,β-Unsaturated aldehydes through the homologation of aldehydes.
c. Vinyl aryl sulfides.
d. 3-Triethylsilyl-3-buten-2-one.
e. α,β-Unsaturated primary amides.
f. Bicyclopentenones.
g. 1-Chlorocyclopropene.
3. Used in Radical Addition Reactions:
Vinyltrimethylsilane is employed in radical addition reactions, such as the addition of α-iodo-α,α-difluoroketones and α-iodosulfones to the compound, leading to the formation of various organic products.
4. Used in Cycloaddition Reactions:
Vinyltrimethylsilane is utilized in 3 + 2 cycloaddition reactions with nitrones, resulting in the formation of diverse heterocyclic compounds.
5. Used in the Formation of Trimethylsilylcyclopropanes:
Vinyltrimethylsilane is used in titanium-mediated reactions to form trimethylsilylcyclopropanes, which are valuable intermediates in organic synthesis.
6. Used as a Hydrogen Acceptor Catalyst:
Vinyltrimethylsilane acts as a hydrogen acceptor catalyst in the conversion of alcohols to hydrogenated Wittig adducts, facilitating the synthesis of various organic compounds.
7. Used in the Synthesis of Trimethylsilylaziridines and Sulfonyl Chlorides:
Vinyltrimethylsilane is employed in the formation of 2-trimethylsilylaziridines and sulfonyl chlorides, which are important building blocks in organic chemistry.
8. Used in the Synthesis of 2-Trimethylsilylethylsulfonyl Chloride:
Vinyltrimethylsilane is used in the improved synthesis of 2-trimethylsilylethylsulfonyl chloride, a valuable reagent in organic synthesis.
9. Used in the Formation of Iron Carbonyl Trienone Complexes:
Vinyltrimethylsilane is utilized in the formation of an iron carbonyl trienone complex, which has potential applications in catalysis and materials science.
10. Used in the Synthesis of 2-Phenyl-2-Trimethylsilylethanol and 2-Vinylanilines:
Vinyltrimethylsilane is employed in the synthesis of 2-phenyl-2-trimethylsilylethanol and 2-vinylanilines, which are important intermediates in the pharmaceutical and agrochemical industries.
11. Used in Decarbonylative Vinylation of Aromatic Esters:
Vinyltrimethylsilane is used in the decarbonylative vinylation of aromatic esters, a key reaction in the synthesis of various organic compounds.
12. Used in Asymmetric Epoxidation:
Vinyltrimethylsilane is employed in asymmetric epoxidation reactions, which are essential for the synthesis of enantiomerically pure compounds.
13. Used in Direct Silylation of Heteroarylcarbonyl Compounds:
Vinyltrimethylsilane is used in the direct silylation of heteroarylcarbonyl compounds, providing a convenient route to various organosilicon heterocycles.
14. Used in Trimethylsilylation of Vinylboronates:
Vinyltrimethylsilane is utilized in the trimethylsilylation of vinylboronates, which are important intermediates in the synthesis of organosilicon compounds.
Preparation
Prepared in 67–91% yield from vinylmagnesium bromide and chlorotrimethylsilane in THF.
Flammability and Explosibility
Flammable
Purification Methods
If the 1H NMR spectrum shows impurities, then dissolve it in Et2O, wash it with aqueous NH4Cl solution, dry over CaCl2, filter, evaporate and distil it at atmospheric pressure in an inert atmosphere. It is used as a co-polymer and may polymerise in the presence of free radicals. It is soluble in CH2Cl2. [Nagel & Post J Org Chem 17 1379 1952, Beilstein 4 IV 3922.]
Check Digit Verification of cas no
The CAS Registry Mumber 754-05-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,5 and 4 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 754-05:
(5*7)+(4*5)+(3*4)+(2*0)+(1*5)=72
72 % 10 = 2
So 754-05-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H12Si/c1-5-6(2,3)4/h5H,1H2,2-4H3
754-05-2Relevant articles and documents
Radiolytic silylation of alkenes and alkynes by gaseous R3Si+ ions. Stereochemical evidence for the β-silyl effect
Chiavarino, Barbara,Crestoni, Maria Elisa,Fornarini, Simonetta
, p. 1523 - 1527 (1998)
Carbocation intermediate stabilized by a β silyl group have been characterized using the silylation of alkenes by R3Si+ ions as a route of formation. Neutral silylated products have been obtained from the reaction of R3Si+ ions, generated in a gaseous medium at atmospheric pressure by a radiolytic technique, with selected alkenes, alkynes, and allene, thereby indicating the occurrence of electrophilic silylation. Notable fectures of the charged silylated intermediates emerge from the isomeric product distribution. The silylation of cis- and trans-2-butene shows a high degree of retention of configuration, as expected if a bridged species (I) were the reaction intermediate. Alternatively, the intermediacy of an open structure (II), whereby C-C bond rotation is inhibited by the hyperconjugative interaction between the β silyl group and the vacant up orbital, should be inferred. The charged intermediates from the silylation of alkenes and alkynes are found to be unreactive toward conceivable isomerizations to more stable species, such as the ones bearing the positive charge of silicon. Stereoelectronic factors affect the deprotonation of the silylated intermediates, which may involves loss of the proton either the α or the γ position with respect to the silylated carbon. A comparison of the reactivity of alkenes and alkynes in the cationic silylation reaction is presented.
Trimethylsilylacetylene synthesis process
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Paragraph 0021, (2021/01/11)
The invention discloses a process route for synthesizing trimethylsilylacetylene, which comprises the following steps of: generating trimethylchlorosilylethylene by taking ethylene bromide and trimethylchlorosilane as initial raw materials through a Grignard method, and forming 1-bromo trimethylchlorosilylethylene under the action of alkali through a bromination reagent; and removing monomolecularhydrogen bromide under the action of strong alkali to generate trimethylsilylacetylene. Compared with the traditional process, the process route has the advantages that the use of gas acetylene is avoided, the risk is reduced, the safety is improved, the used raw materials are easily available, the operation is easy, the safety and the environmental protection are realized, and the industrial production can be realized.
Vanadium-Catalyzed Cross Metathesis: Limitations and Implications for Future Catalyst Design
Farrell, Wesley S.
supporting information, p. 3481 - 3485 (2019/11/13)
Self-metathesis of terminal olefins using vanadium(V) alkylidenes is presented. Under various reaction conditions, incomplete conversion is observed due to decomposition of the metallocyclobutane intermediate via β-hydride elimination. The activity was observed to decline when a more electron withdrawing, less sterically bulky ligand was used, in contrast to trends observed in ring-opening metathesis polymerization with vanadium catalysts. These results provide insight into the current limitations of olefin metathesis with vanadium catalysts, as well as guidance for catalyst development.
Cobalt-catalyzed hydrosilation/hydrogen-transfer cascade reaction: A new route to silyl enol ethers
Lyons, Thomas W.,Brookhart, Maurice
supporting information, p. 10124 - 10127 (2013/09/02)
Capitalizing on cobalt: A new route to silyl enol ethers employing a Co-catalyzed cascade reaction featuring a tandem hydrosilation/hydrogen-transfer reaction is reported. The low catalyst loading, mild reaction conditions, and unique η2-silane resting state showcase the impressive utility of this seldom used transition-metal catalyst in C-H activation reactions (see scheme; VTMS = vinyltrimethylsilane; Cp* = 1,2,3,4,5- pentamethylcyclopentadiene). Copyright
