Ethenone, (trimethylsilyl)-

Base Information

• Chemical Name: Ethenone, (trimethylsilyl)-
• CAS No.: 4071-85-6
• Molecular Formula: C5H10OSi
• Molecular Weight: 114.219
• Hs Code.: 2931900090
• European Community (EC) Number: 620-609-0
• DSSTox Substance ID: DTXSID5063285
• Nikkaji Number: J274.720K
• Mol file: 4071-85-6.mol

Synonyms:TRIMETHYLSILYLKETENE;4071-85-6;Ethenone, (trimethylsilyl)-;(Trimethylsilyl)ketene;Ethenone, 2-(trimethylsilyl)-;2-(trimethylsilyl)ethenone;trimethylsilyl ketene;C5H10OSi;C5-H10-O-Si;SCHEMBL4476192;DTXSID5063285

Chemical Property of Ethenone, (trimethylsilyl)-

Chemical Property:

• Vapor Pressure: 81.2mmHg at 25°C
• Refractive Index: n20/D 1.413(lit.)
• Boiling Point: 81.7 °C at 760 mmHg
• Flash Point: 3.2 °C
• PSA: 17.07000
• Density: 0.813
• LogP: 1.25160
• Solubility.: Sol CH2Cl2, CHCl3, CCl4, THF, diethyl ether, and most standard organic solvents; reacts with alcoholic and amine solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 114.050091473
• Heavy Atom Count: 7
• Complexity: 95.1

Purity/Quality:

98%Min ^*data from raw suppliers

TRIMETHYLSILYLKETENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 7/9-16-29-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)C=C=O
• Physical properties: bp 81–82 °C; d 0.80 g cm?3.
• Uses: Trimethylsilylketene is a reactive acylating agent for amines and alcohols; building block for synthesis of coumarins; synthesis of α-silyl ketones via the addition of organocerium reagents; treatment with stabilized ylides forms trimethylsilyl-substituted allenes;a cycloaddition with aldehydes affords β-lactones; forms small rings with diazomethane; treatment with n-BuLi forms a ketene enolate. It participates in the reactions of Trimethylsilylacetylation of Alcohols and Amines, Synthesis of Coumarins via Cyclization–Elimination, One-pot Formation of α-Silyl Ketones, Preparation of Trimethylsilyl-Substituted Allenes, Preparation of β-Lactones, Reaction with Diazomethane to Form Silylated Cyclopropanes and Cyclobutanones, Synthesis of Heterocycles, Formation of the Ketene Enolate, and other uses.

Technology Process of Ethenone, (trimethylsilyl)-

There total 9 articles about Ethenone, (trimethylsilyl)- 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: 92.0%

2-trimethylsilyl-ethoxyacetylene (1026530-72-2) → trimetylsilylketene (4071-85-6)

Guidance literature:

under 760 Torr; Heating;

DOI:10.1021/ol016096z

Reference yield: 82.0%

ethyl tributylstannyltriethylsilyl acetate + dibutylchloroborane (1730-69-4) → trimetylsilylketene (4071-85-6) + dibutylborinic acid methyl ester (2344-21-0) + tributyltin chloride (1461-22-9)

Guidance literature:

In pentane; -50°C; fractionation;

Reference yield: 70.0%

chloro-trimethyl-silane (75-77-4) + 1-ethoxyacetylene (927-80-0) → trimetylsilylketene (4071-85-6)

Guidance literature:

1-ethoxyacetylene; With methyllithium; In diethyl ether; at 0 ℃; for 0.5h;

chloro-trimethyl-silane; In diethyl ether; at 20 ℃; for 12h;

DOI:10.1081/SCC-120004861

upstream raw materials:

trimethylsilylethoxyacetylene

(trimethylsilyl)acetyl chloride

chloro-trimethyl-silane

1-ethoxyacetylene

Downstream raw materials:

methyl (trimethylsilyl)acetate

C₇H₁₅NO₂Si

trimethylsilyl hexanoate

α-trimethylsilyl trimethylsilylacetic ester

Refernces

• 1、 Black, T. Howard,Farrell, John R.,Probst, Donald A.,Zotz, Michael C.. "A high yielding, reproducible synthesis of trimethylsilylketene". . p. 2083 - 2088. Retrieved 2002.
• 2、 Forslund, Raymond E.,Cain, James,Colyer, John,Doyle, Michael P.. "Chiral dirhodium(II) carboxamidate-catalyzed [2 + 2]-cycloaddition of TMS-ketene and ethyl glyoxylate". . p. 87 - 92. Retrieved 2007/10/03.