17728-88-0

Basic information

• Product Name: ETHYL 3-(TRIMETHYLSILYL)PROPIONATE
• Synonyms: Propanoic acid,3-(trimethylsilyl)-, ethyl ester;ETHYL 3-(TRIMETHYLSILYL)PROPIONATE
• CAS NO: 17728-88-0
• Molecular Formula: C₈H₁₈O₂Si
• Molecular Weight: 174.31
• Product Categories: C8 to C9;Carbonyl Compounds;Esters
• Mol File: 17728-88-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 178-180 °C
• Flash Point: 53 °C
• Appearance: /
• Density: 0.878 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.420
• CAS DataBase Reference: ETHYL 3-(TRIMETHYLSILYL)PROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-(TRIMETHYLSILYL)PROPIONATE(17728-88-0)
• EPA Substance Registry System: ETHYL 3-(TRIMETHYLSILYL)PROPIONATE(17728-88-0)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 17728-88-0(Hazardous Substances Data)

Usage

Purification Methods

Dissolve it in Et2O, wash this with H2O, dilute Na2CO3, dry (Na2SO4), evaporate Et2O and fractionally distil. [Sommer & Marans J Am Chem Soc 72 1935 1950, Beilstein 4 IV 3975.]

Upstream product

• 4206-67-1 iodo(trimethylsilyl)methane 
• 141-97-9 ethyl acetoacetate 
• 75-77-4 chloro-trimethyl-silane 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 140-88-5 ethyl acrylate 
• 109-94-4 formic acid ethyl ester 
• 754-05-2 ethenyltrimethylsilane 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 996-82-7 sodium diethylmalonate 
• 2344-80-1 Chloromethyltrimethylsilane 

Downstream Products

• 5683-30-7 3-trimethylsilylpropionic acid 
• 124871-60-9 ethyl (1RS,3RS,4S,5R,6R,7R)-6,7-dimethyl-3-hydroxy-7-(4-methoxybenzyloxy)-5,6-<1-(4-methoxyphenyl)ethylidenedioxy>-2-trimethylsilyl-methylnonanoate 
• 245764-70-9 4-(trimethylsilyl)-2-methyl-d3-2-butanol-1,1,1-d3 
• 54815-42-8 2-((1S,2R)-2-Hydroxy-cyclohexyl)-acrylic acid ethyl ester 
• 54815-42-8 2-((1S,2S)-2-Hydroxy-cyclohexyl)-acrylic acid ethyl ester 
• 74976-84-4 ethyl 2-(trimethylsilylmethyl)acrylate 
• 124871-68-7 ((2R,3R)-3-{(S)-1-[(4R,5R)-5-[(R)-1-(4-Methoxy-benzyloxy)-propyl]-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2-trimethylsilanylmethyl-oxiranyl)-methanol 
• 124895-76-7 (2E,4S,5R,6R,7R)-4,6-dimethyl-7-(4-methoxybenzyloxy)-5,6-<1-(4-methoxyphenyl)ethylidenedioxy>-2-trimethylsilylmethylnon-2-en-1-ol 
• 124871-67-6 ethyl (2E,4S,5R,6R,7R)-4,6-dimethyl-7-(4-methoxybenzyloxy)-5,6-<1-(4-methoxyphenyl)ethylidenedioxy>-2-trimethylsilylmethyl-2-nonenoate 
• 124871-64-3 (R)-3-Methanesulfonyloxy-4-[(4R,5R)-5-[(R)-1-(4-methoxy-benzyloxy)-propyl]-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-2-trimethylsilanylmethyl-pentanoic acid ethyl ester 
• 80360-96-9 (3aR,4R,7R,7aS)-2-Benzoyl-3-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one 
• 80360-98-1 (3aS,4R,7R,7aR)-2-Benzoyl-3-benzyl-7-[(E)-4-(tert-butyl-dimethyl-silanyl)-but-1-enyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one 
• 80361-16-6 (3aR,4S,5R,6S,7S,7aR)-2-Benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-5,6-dihydroxy-4-methyl-5-trimethylsilanylmethyl-octahydro-isoindol-1-one 
• 80361-17-7 Acetic acid (3aR,4S,5R,6S,7S,7aR)-6-acetoxy-2-benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-1-oxo-5-trimethylsilanylmethyl-octahydro-isoindol-5-yl ester 

Relevant articles and documents

γ-Silyl-stabilized tertiary ions? Solvolysis of 4-(trimethylsilyl)-2-chloro-2-methylbutane

Rate constant, isotope-effect, and product studies of the solvolysis of 4-(trimethylsilyl)-2-chloro-2-methylbutane, 11, and its carbon analog, 2-chloro-2,5,5-trimethylhexane, 10, in aqueous ethanol and aqueous 2,2,2-trifluoroethanol (TFE) indicate very little participation of the γ-silyl substituent. These results are in sharp contrast to earlier reports on secondary γ-silyl substituted systems, in which the back lobe of the silicon-carbon bond has been shown to overlap with the carbocation p-orbital to form a so-called 'percaudally' stabilized intermediate. While the solvolytic behaviors of 11 and 10 are nearly identical in ethanol, differences in the TFE lead to the conclusion that there is a minor amount of participation by the silyl substituent in that solvent. Interestingly, this observation lends credence to an earlier suggestion that TFE is better than ethanol at stabilizing more highly delocalized ions. Copyright

The Highly Regioselective Carbonylation of Vinylsilanes

The hydroesterification of vinylsilanes, catalyzed by transition-metal complexes, afforded both β-silyl esters 2 and α-silyl esters 3 in high yield.The Pd(II) complex-catalyzed reaction showed high β-regioselectivity, whereas the Co2(CO)8-catalyzed reaction showed high α-regioselectivity.Vinylsilanes which bore trialkyl-, diphenylmethyl-, dimethylethoxy-, trimethoxy-, diphenylfluoro-, and difluorophenylsilyl groups were regioselectively, and in some cases regiospecifically, hydroesterified.Pd(II) complexes were also shown to be effective catalysts of the hydrocarboxylation of vinylsilanes.Hydrocarboxylation was β-regiospecific and gave excellent yields of β-silyl carboxylic acids.Reasonable mechanisms for the reactions are described.

RADICAL REACTIONS OF 1,1-DIETHOXYMETHANE AND ETHYL FORMATE WITH TRIMETHYLVINYLSILANE

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