72047-94-0

Basic information

• Product Name: 2-(Trimethylsilylmethyl)allyl acetate
• Synonyms: 2-(ACETOXYMETHYL)-3-(TRIMETHYLSILYL)PROPENE;[2-(ACETOXYMETHYL)ALLYL]TRIMETHYLSILANE;2-(ACETOXYMETHYL)ALLYTRIMETHYLSILANE;2-[(TRIMETHYLSILYL)METHYL]-2-PROPEN-1-VL ACETATE;2-[(TRIMETHYLSILYL)METHYL]-2-PROPEN-1-YL ACETATE;2-(TRIMETHYLSILYLMETHYL)ALLYL ACETATE;3-ACETOXY-2-(TRIMETHYLSILYLMETHYL)-1-PROPENE;2-(Acetoxymethyl)allyltrimethyliane
• CAS NO: 72047-94-0
• Molecular Formula: C₉H₁₈O₂Si
• Molecular Weight: 186.32
• Mol File: 72047-94-0.mol

Chemical Properties

• Boiling Point: 95 °C7 mm Hg(lit.)
• Flash Point: 160 °F
• Appearance: Clear colorless/Liquid
• Density: 0.877 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.074mmHg at 25°C
• Refractive Index: n20/D 1.440(lit.)
• Storage Temp.: 2-8°C
• Solubility: Solubility most organic solvents.
• Water Solubility: reacts
• BRN: 1933657
• CAS DataBase Reference: 2-(Trimethylsilylmethyl)allyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trimethylsilylmethyl)allyl acetate(72047-94-0)
• EPA Substance Registry System: 2-(Trimethylsilylmethyl)allyl acetate(72047-94-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-14
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• Hazardous Substances Data: 72047-94-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-(Trimethylsilylmethyl)allyl acetate is used as a reagent in the synthesis of cyclopentane derivatives through Pd(0)-catalyzed reactions with 2π acceptors. Its unique structure allows for the formation of complex molecular architectures, which are valuable in various chemical and pharmaceutical applications.
Used in Organic Chemistry:
As a precursor for palladium trimethylenemethane cycloaddition reactions, 2-(Trimethylsilylmethyl)allyl acetate plays a crucial role in the construction of complex organic molecules. This application is particularly relevant in the fields of medicinal chemistry and materials science, where the development of novel compounds with specific properties is of great interest.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, the compound's reactivity and structural features suggest potential applications in the pharmaceutical industry. It could be used as a building block for the synthesis of bioactive molecules or as an intermediate in the production of pharmaceutical compounds.

Preparation

commercially available but expensive. Several preparations of (1) or the precursor alcohol (2) have been reported. The simplest involves the direct silylation of methallyl alcohol (eq 1).

InChI:InChI=1/C9H18O2Si/c1-8(6-11-9(2)10)7-12(3,4)5/h1,6-7H2,2-5H3

Upstream product

• 791845-53-9 2-iodoallyl acetate 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 83378-96-5 O-trimethylsilyl-2-(trimethylsilylmethyl)prop-2-en-1-ol 
• 81302-80-9 2-(trimethylsilylmethyl)prop-2-en-1-ol 
• 75-36-5 acetyl chloride 
• 917-54-4 methyllithium 
• 126386-39-8 1-Oxa-2-silacyclopentane 
• 18388-03-9 2-chloromethyl-3-trimethylsilyl-1-propene 
• 127-08-2 potassium acetate 

Downstream Products

• 122491-06-9 Spiro<<2-(R)-<(benzoyloxy)methyl>-4-(R)-ethoxy-3-oxacyclohexane>-1,2'-(R)-(4'-methylenetetrahydrofuran)> 
• 122491-06-9 Spiro<<2-(R)-<(benzoyloxy)methyl>-4-(R)-ethoxy-3-oxacyclohexane>-1,2'-(S)-(4'-methylenetetrahydrofuran)> 
• 99583-47-8 2-(4-Isopropenyl-cyclohex-1-enyl)-4-methylene-tetrahydro-furan 
• 107841-75-8 (2-Methylene-1,2,3,4,7,7a-hexahydro-4,7-methano-inden-3a-yl)-phenyl-methanone 
• 122491-17-2 2-(2'-Benzofuryl)-2-phenyl-4-methylenetetrahydrofuran 
• 122491-08-1 7-(Benzyloxy)-2-methylene-4-oxo-6-oxaperhydroindane 
• 122491-09-2 Spiro<<4(R^*)-(benzyloxy)-3-oxacyclohex-5-ene>-1,2'(S^*)-(4-methylenetetrahydrofuran)> 
• 72047-98-4 methyl trans-2-phenyl-4-methylenecyclopentane-1-carboxylate 
• 72047-99-5 methyl cis-2-phenyl-4-methylenecyclopentane-1-carboxylate 
• 398137-91-2 (R)-2-benzyl-5-methylene-1-(toluene-4-sulfonyl)-piperidine 
• 398137-88-7 (R)-2-propyl-5-methylene-1-(4-methoxy-benzenesulfonyl)-piperidine 
• 616866-52-5 2(S)-[2-(tert-butyl-dimethyl-silanyloxy)-1(S)-methyl-ethyl]-5-methylene-1-(toluene-4-sulfonyl)-piperidine 

Relevant articles and documents

A Short and Efficient Preparation of 2-Trimethylsilylmethyl-2-propen-1-ol

2-Trimethylsilylmethyl-2-propen-1-ol is efficiently prepared in 64percent overall yield starting from the cheap propargyl alcohol.

Radical cyclization of bromomethyldimethylsilyl propargyl ethers; A general method for the stereoselective synthesis of variously substituted trimethylenemethane (TMM) precursors

The radical cyclization of bromomethyldimethylsilyl propargyl ethers allows the regio- and stereoselective preparation of variously substituted 2- trimethylsilylmethyl-2-propen-1-ol derivatives in good yields. After acetylation of the alcohol function, th

Preparation of 2-(trimethylsilyl)methyl-2-propen-1-ol derivatives by cobalt catalyzed sp2-sp3 coupling

A practical, operationally simple preparation of 2-(trimethylsilyl)methyl-2-propen-1-ol derivatives is described. The cobalt catalyzed coupling of a protected vinyl halide with trimethylsilylmethylmagnesium chloride shows excellent functional group tolerance and provides these synthetically useful allyl silanes in good overall yield. By this method, the use of highly concentrated organolithium reagents, complex reaction protocols, and expensive starting materials is avoided.

Studies in the stereospecific synthesis of sesbanimide. Approaches to ring C

Strating from 2-methylpropenol-2 and dimethyl 2,3-dimethylmaleate model approaches for the syntheses of ring C of sesbanimide and 13-oxo-sesbanimide have been developed