Trimethylsilylketene Ethyl Trimethylsilyl Acetal

Base Information

• Chemical Name: Trimethylsilylketene Ethyl Trimethylsilyl Acetal
• CAS No.: 65946-56-7
• Molecular Formula: C10H24O2Si2
• Molecular Weight: 232.47
• European Community (EC) Number: 672-605-3
• Nikkaji Number: J2.731.680H,J531.779G
• Wikidata: Q76422097
• Mol file: 65946-56-7.mol

Synonyms:65946-56-7;Trimethylsilylketene Ethyl Trimethylsilyl Acetal;[(E)-1-ethoxy-2-trimethylsilylethenoxy]-trimethylsilane;TrimethylsilylketeneEthylTrimethylsilylAcetal;T72791;{[(1E)-1-ethoxy-2-(trimethylsilyl)ethenyl]oxy}trimethylsilane;Trimethylsilylketene ethyl trimethylsilyl acetal(mixture of isomers)

Chemical Property of Trimethylsilylketene Ethyl Trimethylsilyl Acetal

Chemical Property:

• Vapor Pressure: 0.61mmHg at 25°C
• Boiling Point: 194.679oC at 760 mmHg
• Flash Point: 61.373oC
• PSA: 18.46000
• Density: 0.857g/cm3
• LogP: 3.59320
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 232.13148307
• Heavy Atom Count: 14
• Complexity: 199

Purity/Quality:

98%,99%, ^*data from raw suppliers

TrimethylsilylketeneEthylTrimethylsilylAcetal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=C[Si](C)(C)C)O[Si](C)(C)C
• Isomeric SMILES: CCO/C(=C\[Si](C)(C)C)/O[Si](C)(C)C
• Use Description: Trimethylsilylketene ethyl trimethylsilyl acetal, a chemical mixture of isomers, has various applications across different fields. In the field of organic synthesis, it serves as a versatile reagent for the preparation of complex organic molecules, including pharmaceuticals, agrochemicals, and fine chemicals. Its role as a synthetic intermediate enables the efficient creation of diverse chemical structures with precise control over functional groups. In the realm of materials science, it can be employed in the development of specialized materials, coatings, and polymers with unique properties, offering opportunities for the design of innovative materials for various applications. Additionally, in the pharmaceutical industry, it may find use as a starting material for the synthesis of drug compounds, contributing to drug discovery and development. Its versatility as a reagent and building block underscores its significance in organic synthesis, materials science, and pharmaceutical research, playing crucial roles in advancing research and innovation in these diverse fields.

Technology Process of Trimethylsilylketene Ethyl Trimethylsilyl Acetal

There total 3 articles about Trimethylsilylketene Ethyl Trimethylsilyl Acetal 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: 93.0%

trimethylsilanyl-acetic acid ethyl ester (4071-88-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-ethoxy-1-(trimethylsiloxy)-2-(trimethylsilyl)ethene (65946-56-7)

Guidance literature:

trimethylsilanyl-acetic acid ethyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at -78 ℃; Further stages.;

DOI:10.1246/cl.2008.704

Reference yield: 85.0%

chloro-trimethyl-silane (75-77-4) + trimethylsilanyl-acetic acid ethyl ester (4071-88-9) → 1-ethoxy-1-(trimethylsiloxy)-2-(trimethylsilyl)ethene (65946-56-7)

Guidance literature:

With lithium diisopropyl amide; 1.) -78 deg C, 3 h; 2.) RT, 1.5 h;

DOI:10.1016/0022-328X(87)80302-9

Reference yield: 44.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + ethyl acetate (141-78-6) → trimethylsilanyl-acetic acid ethyl ester (4071-88-9) + 1-ethoxy-1-(trimethylsiloxy)-2-(trimethylsilyl)ethene (65946-56-7) + 2,2-Bis(trimethylsilyl)ethansaeure-ethylester (65946-55-6)

Guidance literature:

With triethylamine; In diethyl ether; for 2h; Yields of byproduct given; Ambient temperature;

upstream raw materials:

chloro-trimethyl-silane

trimethylsilanyl-acetic acid ethyl ester

trimethylsilyl trifluoromethanesulfonate

ethyl acetate

Downstream raw materials:

ethyl (E)-3-(pyridin-3-yl)acrylate

ethyl (E)-3-(4-chlorophenyl)prop-2-enoate

(E)-ethyl 2-chlorocinnamate

ethyl 3-phenyl-2-propenoate

Refernces

• 1、 Hazelard, Damien,Ollivier, Jean,Paugam, Renée,Salaün, Jacques. "Formation of 1-ethenylcyclopropanols involving Kulinkovich cyclopropanation and Peterson olefination of α-trimethylsilylesters". . p. 1155 - 1159. Retrieved 2007/10/03.
• 2、 Emde, Herbert,Simchen, Gerhard. "Reactions of Trialkylsilyl Trifluoromethanesulfonates, II. - Synthesis of O-Alkyl-O-(trialkylsilyl)ketene Acetals and 2-(Trialkylsilyl)carboxylates". . p. 816 - 834. Retrieved 2007/10/02.