18269-31-3 Usage
Description
METHYL (1-TRIMETHYLSILYL)ACRYLATE is a versatile chemical compound that serves as a reactive α-silyl Michael acceptor in various organic synthesis processes. It is characterized by its ability to undergo conjugate addition with carbanions, enolate anions, organolithium reagents, and Grignard reagents, leading to the formation of 3-cyclopentenecarboxylates and cyclohexanecarboxylates through [3 + 2] and [4 + 2] annulation methods. Additionally, it can be used to produce α-silyl esters and vinylsilanes through organolithium conjugate additions. METHYL (1-TRIMETHYLSILYL)ACRYLATE exhibits physical properties such as a boiling point of 75 °C at 50 mmHg and 152 °C at 690 mmHg.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 18269-31-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,2,6 and 9 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 18269-31:
(7*1)+(6*8)+(5*2)+(4*6)+(3*9)+(2*3)+(1*1)=123
123 % 10 = 3
So 18269-31-3 is a valid CAS Registry Number.
18269-31-3Relevant articles and documents
2-pyrimidylphosphines: A new class of ligands for transition metal catalysis
Reetz, Manfred T.,Demuth, Ralf,Goddard, Richard
, p. 7089 - 7092 (1998)
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
1,3-DIPOLAR CYCLOADDITION OF BENZONITRILE OXIDE WITH VINYLSILANES
Padwa, Albert,MacDonald, J. Gavin
, p. 3219 - 3222 (2007/10/02)
The reaction of benzonitrile oxide with several vinylsilanes has been found to afford silylated isoxazoles.Relative rates for the cycloaddition reaction were determined.
