METHYL (1-TRIMETHYLSILYL)ACRYLATE

Base Information

• Chemical Name: METHYL (1-TRIMETHYLSILYL)ACRYLATE
• CAS No.: 18269-31-3
• Molecular Formula: C7H14 O2 Si
• Molecular Weight: 158.27
• Hs Code.: 2931900090
• Mol file: 18269-31-3.mol

Synonyms:Acrylicacid, 2-(trimethylsilyl)-, methyl ester (7CI,8CI); Methyl2-(trimethylsilyl)acrylate; Methyl 2-trimethylsilyl-2-propenoate; Methyl a-(trimethylsilyl)acrylate

Chemical Property of METHYL (1-TRIMETHYLSILYL)ACRYLATE

Chemical Property:

• Boiling Point: 75 °C
• PSA: 26.30000
• LogP: 1.59300
• Solubility.: sol Et2O, THF, EtOH, and most organic solvents.

Purity/Quality:

97% ^*data from raw suppliers

METHYL (1-TRIMETHYLSILYL)ACRYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Physical properties: bp 75 °C/50 mmHg, 152 °C/690 mmHg.
• Uses: Methyl 2-Trimethylsilylacrylate is widely used as reactive, α-silyl Michael acceptor for conjugate addition of carbanions, enolate anions, organolithium reagents, and Grignard reagents; affords 3-cyclopentenecarboxylates and cyclohexanecarboxylates by [3 + 2] and [4 + 2] annulation methods; provides α-silyl esters and vinylsilanes by organolithium conjugate additions.

Technology Process of METHYL (1-TRIMETHYLSILYL)ACRYLATE

There total 4 articles about METHYL (1-TRIMETHYLSILYL)ACRYLATE 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: 65.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + trimethylsilylacetylene (1066-54-2) → Methyl α-(trimethylsilyl)acrylate (18269-31-3)

Guidance literature:

With methanesulfonic acid; palladium diacetate; diphenyl-(6-methyl-pyridin-2-yl)phosphine; at 60 ℃; for 3h; under 22801.5 Torr; Inert atmosphere; Autoclave;

DOI:10.1002/aoc.6391

Reference yield:

methanol (67-56-1) + carbon monoxide (201230-82-2) + trimethylsilylacetylene (1066-54-2) → Methyl α-(trimethylsilyl)acrylate (18269-31-3) + methyl 3-(trimethylsilyl)acrylate (292822-45-8)

Guidance literature:

With methanesulfonic acid; palladium diacetate; diphenyl-(6-methyl-pyridin-2-yl)phosphine; at 60 ℃; for 3h; under 22801.5 Torr; Inert atmosphere; Autoclave;

DOI:10.1002/aoc.6391

Reference yield:

methanol (67-56-1) + 2-trimethylsilanyl-acrylic acid (18187-17-2) → Methyl α-(trimethylsilyl)acrylate (18269-31-3)

Guidance literature:

With sulfuric acid; Heating;

DOI:10.1139/v63-437

upstream raw materials:

diazomethane

2-trimethylsilanyl-acrylic acid

methanol

carbon monoxide

Downstream raw materials:

methyl (Z)-2-cinnamylidene-4-methylene-5-hexenoate

methyl (E)-2-cinnamylidene-4-methylene-5-hexenoate

methyl 2-<2-methylsulfinyl-2-(methylthio)ethyl>-5-phenyl-2,4-pentadienoate

methyl (2Z,4E) 2-benzyl-5-phenyl-2,4-pentadienoate