ETHYL 3-(TRIMETHYLSILYL)PROPIOLATE

Base Information

• Chemical Name: ETHYL 3-(TRIMETHYLSILYL)PROPIOLATE
• CAS No.: 16205-84-8
• Molecular Formula: C8H14O2Si
• Molecular Weight: 170.283
• Hs Code.: 29310099
• Mol file: 16205-84-8.mol

Synonyms:Propiolicacid, (trimethylsilyl)-, ethyl ester (6CI,8CI);1-(Ethoxycarbonyl)-2-(trimethylsilyl)acetylene;3-(Trimethylsilyl)-2-propynoicacid ethyl ester;Ethyl (trimethylsilyl)ethynylcarboxylate;Ethyl(trimethylsilyl)propiolate;Ethyl 3-(trimethylsilyl)propiolate;Ethyl3-(trimethylsilyl)propynoate;

Chemical Property of ETHYL 3-(TRIMETHYLSILYL)PROPIOLATE

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 0.53mmHg at 25°C
• Refractive Index: n20/D 1.441(lit.)
• Boiling Point: 190.9 °C at 760 mmHg
• Flash Point: 71.1 °C
• PSA: 26.30000
• Density: 0.929 g/cm³
• LogP: 1.43030
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Sparingly soluble in water.

Purity/Quality:

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

3-(Trimethylsilyl)-2-propynoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 3-(trimethylsilyl)propiolate was used in the preparation of 4-ethoxycarbonyl-3-(trimethylsilyl)furan.

Technology Process of ETHYL 3-(TRIMETHYLSILYL)PROPIOLATE

There total 7 articles about ETHYL 3-(TRIMETHYLSILYL)PROPIOLATE 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: 95.0%

chloroformic acid ethyl ester (541-41-3) + trimethylsilylacetylene (1066-54-2) → ethyl 3-(trimethylsilyl)propynoate (16205-84-8)

Guidance literature:

With n-butyllithium;

DOI:10.1016/S0960-894X(97)00293-X

Reference yield: 95.0%

(trifluoromethyl)trimethylsilane (81290-20-2) + propynoic acid ethyl ester (623-47-2) → ethyl 3-(trimethylsilyl)propynoate (16205-84-8)

Guidance literature:

With sodium hydride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In neat (no solvent); at 31 - 33 ℃; for 0.166667h;

DOI:10.1039/c4ra08727e

Reference yield: 80.0%

ethyl (E)-3-iodopropenoate (31930-36-6,31930-37-7) + trimethylsilylacetylene (1066-54-2) → ethyl 3-(trimethylsilyl)propynoate (16205-84-8)

Guidance literature:

ethyl (E)-3-iodopropenoate; With copper(l) iodide; dichlorobis(tri-O-tolylphosphine)palladium; triethylamine; at 50 ℃;

trimethylsilylacetylene; at 50 ℃; for 12h;

DOI:10.1002/chem.201202701

upstream raw materials:

3-(trimethylsilyl)prop-2-ynoic acid

chloroformic acid ethyl ester

trimethylsilylacetylene

Bis(trimethylsilyl)ethyne

Downstream raw materials:

2-(Ethoxycarbonyl)-1-(trimethylsilyl)benzol

ethyl 3-(diethylamino)acrylate

ethyl (Z)-3-iodopropenoate

ethyl (Z)-3-iodo-3-(trimethylsilyl)propenoate

Refernces

• 1、 Chan, Jessica Z.,Yesilcimen, Ahmet,Cao, Min,Zhang, Yuyang,Zhang, Bochao,Wasa, Masayuki. "Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules". supporting information. p. 16493 - 16505. Retrieved 2020/10/26.
• 2、 Arde, Panjab,Reddy, Virsinha,Anand, Ramasamy Vijaya. "NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions". . p. 49775 - 49779. Retrieved 2014/12/11.