Ethyl (trimethylsilyl)acetate

Base Information

• Chemical Name: Ethyl (trimethylsilyl)acetate
• CAS No.: 4071-88-9
• Molecular Formula: C7H16O2Si
• Molecular Weight: 160.288
• Hs Code.: 29319090
• European Community (EC) Number: 223-783-2
• NSC Number: 108051,234752
• UNII: JJ5WZD3DYT
• DSSTox Substance ID: DTXSID10193694
• Nikkaji Number: J217.879F
• Wikidata: Q72477609
• Mol file: 4071-88-9.mol

Synonyms:4071-88-9;Ethyl (trimethylsilyl)acetate;Ethyl 2-(trimethylsilyl)acetate;Ethyl trimethylsilylacetate;Ethyl (2-trimethylsilyl)acetate;(Trimethylsilyl)acetic Acid Ethyl Ester;ethyl 2-trimethylsilylacetate;ethyl(trimethylsilyl)acetate;ETSA;Acetic acid, (trimethylsilyl)-, ethyl ester;JJ5WZD3DYT;EINECS 223-783-2;NSC-108051;NSC-234752;Ethyl(2-trimethylsilyl)acetate;MFCD00009172;UNII-JJ5WZD3DYT;Ethyltrimethylsilylacetate;ethyl trimethlysilylacetate;SCHEMBL435045;Ethyl2-(trimethylsilyl)acetate;QQFBQBDINHJDMN-UHFFFAOYSA-;DTXSID10193694;Ethyl (2-trimethylsilyl)-acetate;AMY42247;Ethyl trimethylsilylacetate, >=98%;trimethylsilylacetic acid ethyl ester;NSC108051;NSC234752;AKOS015909085;CS-W016151;NSC 108051;NSC 234752;trimethylsilanyl-acetic acid ethyl ester;CS-17372;ETHYL .ALPHA.-(TRIMETHYLSILYL)ACETATE;FT-0625803;T1584;EN300-7402551;2-(TRIMETHYLSILYL)ACETIC ACID ETHYL ESTER;Ethyl trimethylsilylacetate, purum, >=95.0% (GC);ACETIC ACID, 2-(TRIMETHYLSILYL)-, ETHYL ESTER

Chemical Property of Ethyl (trimethylsilyl)acetate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 2.75mmHg at 25°C
• Refractive Index: n20/D 1.415(lit.)
• Boiling Point: 157.5 °C at 760 mmHg
• Flash Point: 35.8 °C
• PSA: 26.30000
• Density: 0.874 g/cm³
• LogP: 1.88770
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Solubility.: sol ethereal and chlorinated solvents; reacts with protic solvents.
• Water Solubility.: Decomposition
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 160.091956283
• Heavy Atom Count: 10
• Complexity: 115

Purity/Quality:

99% ^*data from raw suppliers

Ethyl (Trimethylsilyl)acetate >93.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 16-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C[Si](C)(C)C
• Uses: (silylating agent; source of an ethyl acetate anion equivalent.Ethyl trimethylsilylacetate is reactive to nucleophiles and readily undergoes desilylation reactions with acid or alkali,ethanol, and bromine. Ethyl trimethylsilylacetate is used in the synthesis of ethyl-2,2-dibromo-2-(trimethylsilyl)acetate and α,β-unsaturated esters. It was also used to silylate the enolizable aldehydes and ketones.

Technology Process of Ethyl (trimethylsilyl)acetate

There total 15 articles about Ethyl (trimethylsilyl)acetate 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: 91.0%

chloro-trimethyl-silane (75-77-4) + ethyl bromoacetate (105-36-2) → trimethylsilanyl-acetic acid ethyl ester (4071-88-9)

Guidance literature:

With zinc; In diethyl ether;

DOI:10.1021/jo00174a026

Reference yield: 75.0%

(trimethylsilyl)methylmagnesium chloride (13170-43-9) + chloroformic acid ethyl ester (541-41-3) → trimethylsilanyl-acetic acid ethyl ester (4071-88-9)

Guidance literature:

In diethyl ether;

DOI:10.1021/ja01189a011

Reference yield: 74.0%

ethyl bromoacetate (105-36-2) → trimethylsilanyl-acetic acid ethyl ester (4071-88-9)

Guidance literature:

With chloro-trimethyl-silane; copper(l) chloride; zinc; In tetrahydrofuran; benzene; for 2.5h; Inert atmosphere; Reflux;

DOI:10.1246/cl.160975

upstream raw materials:

(trimethylsilyl)methylmagnesium chloride

chloroformic acid ethyl ester

chloro-trimethyl-silane

ethyl acetate

Downstream raw materials:

ethyl 2-(3-trimethylsiloxycyclohex-2-en-1-yl)acetate

trimethyl(oct-1-yloxy)silane

(Z)-1-phenyl-2-(trimethylsiloxy)propene

chloro-trimethyl-silane

Refernces

• 1、 Lejkowski, Michal,Banerjee, Prabal,Raabe, Gerhard,Runsink, Jan,Gais, Hans-Joachim. "Spiro- and bicycloannulation of sulfoximine-substituted 2-hydroxy-dihydropyrans: Enantioselective synthesis of spiroketals, spiroethers, and oxabicycles and structure of dihydropyran oxocarbenium ions". . p. 529 - 553. Retrieved 2014/02/14.
• 2、 Makioka, Yoshikazu,Taniguchi, Yuki,Takaki, Ken,Fujiwara, Yuzo. "Facile Isomerization of Trimethylsilyl Ketene Acetals to α-Trimethylsilyl Esters Catalyzed by Lanthanoid Trifluoromethanesulfonates". . p. 645 - 648. Retrieved 2007/10/02.