754-05-2 | Vinyltrimethylsilane

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$26.00	$18.00
5g	95%	in stock	$34.00	$24.00
25g	95%	in stock	$89.00	$62.00
100g	95%	in stock	$299.00	$209.00

Description

• Catalog Number: AB47280
• Chemical Name: Vinyltrimethylsilane
• CAS Number: 754-05-2
• Molecular Formula: C5H12Si
• Molecular Weight: 100.2343
• MDL Number: MFCD00008606
• SMILES: C=C[Si](C)(C)C
• NSC Number: 93553

Computed Properties

• Complexity: 49.4
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 6
• Rotatable Bond Count: 1

Upstream Synthesis Route

Vinyltrimethylsilane, a versatile organosilicon compound, is commonly used in chemical synthesis for a wide range of applications. It serves as a valuable building block in organic chemistry, particularly in the preparation of various fine chemicals and pharmaceutical intermediates.In organic synthesis, Vinyltrimethylsilane is frequently employed as a key reagent in the functionalization of diverse organic compounds. Its unique vinyl functional group allows for efficient transformations, including cross-coupling reactions, cycloadditions, and radical additions, leading to the formation of complex molecular structures with high efficiency and selectivity.Additionally, Vinyltrimethylsilane finds significant utility in the preparation of silicon-containing polymers and materials. Its incorporation into polymerization processes imparts desirable properties, such as enhanced flexibility, thermal stability, and compatibility with other organic and inorganic components.Moreover, Vinyltrimethylsilane is utilized in the field of organometallic chemistry for ligand modification, catalysis, and as a precursor to various functionalized organosilicon compounds. Its compatibility with a wide range of functional groups and its ability to participate in diverse chemical reactions make it a valuable asset in the toolbox of synthetic chemists working in academia, pharmaceuticals, and industrial research and development.

Literature

• Iron-catalyzed unexpected easy access to stereodefined trimethylsilyl vinyl ketenes.

  Organic letters 20120817

• (E)-9-(2-iodovinyl)-9H-carbazole: a new coupling reagent for the synthesis of π-conjugated carbazoles.

  Organic letters 20110415

• Room-temperature regioselective C-H/olefin coupling of aromatic ketones using an activated ruthenium catalyst with a carbonyl ligand and structural elucidation of key intermediates.

  Journal of the American Chemical Society 20101222

• Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.

  Journal of the American Chemical Society 20100825

• Cobalt-catalyzed regio- and stereoselective intermolecular enyne coupling: an efficient route to 1,3-diene derivatives.

  Chemical communications (Cambridge, England) 20100321

• Quantum chemical studies on substitution effects within silyl group in the silylative coupling of olefins.

  Journal of molecular modeling 20100301

• Palladium-catalyzed cyclopropanation of alkenyl silanes by diazoalkanes: evidence for a Pd(0) mechanism.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20090101

• Why does fluoride anion accelerate transmetalation between vinylsilane and palladium(II)-vinyl complex? Theoretical study.

  Journal of the American Chemical Society 20081001

• Scope and mechanism of the intermolecular addition of aromatic aldehydes to olefins catalyzed by Rh(I) olefin complexes.

  Journal of the American Chemical Society 20070221

• Part 3. Triethylborane-air: a suitable initiator for intermolecular radical additions of S-2-oxoalkyl-thionocarbonates (S-xanthates) to olefins.

  Beilstein journal of organic chemistry 20070101

• Cobalt-mediated cross-coupling reactions of primary and secondary alkyl halides with 1-(trimethylsilyl)ethenyl- and 2-trimethylsilylethynylmagnesium reagents.

  Organic letters 20060706

• Vinyltrimethylsilane (VTMS) as a probe of chemical reactivity of a TiCN diffusion barrier-covered silicon surface.

  The journal of physical chemistry. B 20060316

• Complex thermal chemistry of vinyltrimethylsilane on Si(100)-2x1.

  The journal of physical chemistry. B 20050505

• Photochemical reactions of [CH2(eta5-C5H4)2][Rh(C2H4)2]2 with silanes: evidence for Si-C and C-H activation pathways.

  Dalton transactions (Cambridge, England : 2003) 20050221

• Cationic carbohydroxylation of alkenes and alkynes using the cation pool method.

  Organic letters 20040805

• Synthesis and structure of polymeric networks of silver hexafluoroacetylacetonate complexes of THF, toluene, and vinyltrimethylsilane.

  Inorganic chemistry 20031215

• Preparation of optically pure propargylic and allylic alcohols from 2-(trimethylsilyl)vinyl sulfoxides as a chiral ethynyl anion synthon: computational studies on elimination reaction of 2-(trimethylsilyl)vinyl sulfoxides.

  The Journal of organic chemistry 20020208

• Trimethylsilyl group migrations in cryogenic ozonolysis of trimethylsilylethene: evidence for nonconcerted primary ozonide decomposition pathway.

  The Journal of organic chemistry 20011019