18269-31-3

Usage

Uses

Used in Organic Synthesis:
METHYL (1-TRIMETHYLSILYL)ACRYLATE is used as a reactive α-silyl Michael acceptor for the conjugate addition of carbanions, enolate anions, organolithium reagents, and Grignard reagents. This allows for the formation of various cyclic compounds, such as 3-cyclopentenecarboxylates and cyclohexanecarboxylates, through [3 + 2] and [4 + 2] annulation methods.
Used in the Production of α-Silyl Esters and Vinylsilanes:
METHYL (1-TRIMETHYLSILYL)ACRYLATE is utilized as a precursor in the synthesis of α-silyl esters and vinylsilanes through organolithium conjugate additions. These compounds are valuable intermediates in the development of new materials and pharmaceuticals.
Used in Pharmaceutical Industry:
METHYL (1-TRIMETHYLSILYL)ACRYLATE is used as a key intermediate in the synthesis of various pharmaceutical compounds, owing to its ability to form a wide range of cyclic and acyclic structures through its reactive nature.
Used in Material Science:
METHYL (1-TRIMETHYLSILYL)ACRYLATE is employed in the development of new materials, such as polymers and coatings, due to its versatility in forming different types of chemical structures and its compatibility with various reaction conditions.

Preparation

Methyl 2-Trimethylsilylacrylate is prepared by the reaction of (E)-2- (trimethylsilyl)vinyllithium with methyl chloroformate or by carbonation of the corresponding Grignard reagent prepared from (1-bromovinyl)trimethylsilane, giving 2-trimethylsilylacrylic acid. The methyl ester is prepared from the acid by direct esterification with absolute methanol in the presence of mineral acid, by reaction with diazomethane at low temperature, or by treatment with BF3·MeOH complex.

Upstream product

• 186581-53-3 diazomethane 
• 18187-17-2 2-trimethylsilanyl-acrylic acid 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 95450-25-2 methyl (Z)-2-cinnamylidene-4-methylene-5-hexenoate 
• 95450-24-1 methyl (E)-2-cinnamylidene-4-methylene-5-hexenoate 
• 95450-29-6 methyl 2-<2-methylsulfinyl-2-(methylthio)ethyl>-5-phenyl-2,4-pentadienoate 
• 95450-16-1 methyl (2Z,4E) 2-benzyl-5-phenyl-2,4-pentadienoate 
• 95450-15-0 methyl (2E,4E) 2-benzyl-5-phenyl-2,4-pentadienoate 
• 95450-18-3 methyl (2Z,4E)-2-benzyl-2,4-hexadienoate 
• 95450-17-2 methyl (2E,4E)-2-benzyl-2,4-hexadienoate 
• 80536-55-6 6,7-Dimethoxy-2-trimethylsilanyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester 
• 80536-54-5 2-[2-(2-Bromo-ethyl)-4,5-dimethoxy-benzyl]-pentanedioic acid dimethyl ester 
• 125620-36-2 dimethyl 2-benzyl-2,4-bis(trimethylsilyl)pentanedioate 
• 125620-36-2 dimethyl 2-benzyl-2,4-bis(trimethylsilyl)pentanedioate 
• 95450-20-7 methyl 2-cyclohexylidene-3-phenylpropanoate 
• 84297-13-2 (Z)-2-benzyl-3-phenylacrylic acid methyl ester 
• 128059-71-2 5-ethyl 1-methyl 2-benzylidene-4-(trimethylsilyl)pentanedioate 

Relevant academic research and scientific papers

2-pyrimidylphosphines: A new class of ligands for transition metal catalysis

The synthesis of 2-pyrimidyldiphenylphosphine (2), bis-2- pyrimidylphenyl-phosphine (3) and tris-2-pyrimidylphosphine (4) is described. Ligand 2 forms cationic complexes with palladium(II) in which four-membered P/N-chelates are involved, leading to a ver

The intriguing methoxycarbonylation of trimethylsilylacetylene in the presence of Drent's catalytic system

The alkoxycarbonylation of trimethylsilylacetylene has been studied in order to develop an atom economic sustainable synthesis of 2-(trimethylsilyl)acrylates, a family of valuable intermediates. Pd(OAc)2 in combination with CH3SO3H and diphenyl-(pyridin-2-yl)phosphine or diphenyl-(6-methyl-pyridin-2-yl)phosphine is an active catalyst for the reaction affording mixtures of the sought 2-(trimethylsilyl)acrylate and the isomeric 3-(trimethylsilyl)acrylate. The phosphine ligand has a dramatic effect on the reaction. When employing diphenyl-(pyridin-2-yl)phosphine, it is necessary to carry out the reaction at 80°C in order to observe a modest catalytic activity, and the product is an almost equimolecular mixture of the two isomeric esters. On the contrary, when employing diphenyl-(6-methyl-pyridin-2-yl)phosphine, the reaction proceeds under much milder conditions affording with high rate (turnover frequency [TOF] up to 1200 h?1) and selectivity (>95%) of the sought 2-(trimethylsilyl)acrylate. The reaction conditions have been optimized, and the effects of phosphine/palladium, acid/palladium, reaction time, temperature, and CO pressure have been investigated.

1,3-DIPOLAR CYCLOADDITION OF BENZONITRILE OXIDE WITH VINYLSILANES

The reaction of benzonitrile oxide with several vinylsilanes has been found to afford silylated isoxazoles.Relative rates for the cycloaddition reaction were determined.