13411-48-8

Basic information

• Product Name: ACETYLTRIMETHYLSILANE
• Synonyms: 1-(TRIMETHYLSILYL)ETHANONE;ACETYLTRIMETHYLSILANE;ACETYLTRIMETHYLSILAN;1-TRIMETHYLSILANYL-ETHANONE;Acetyltrimethylsilane,1-(Trimethylsilyl)ethanone;Silane,acetyltrimethyl-
• CAS NO: 13411-48-8
• Molecular Formula: C₅H₁₂OSi
• Molecular Weight: 116.23
• EINECS: 220-404-2
• Mol File: 13411-48-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: <0℃
• Boiling Point: 113-114°C
• Flash Point: 48 °F
• Appearance: /
• Density: 0.811 g/mL at 25 °C(lit.)
• Vapor Pressure: 19.3mmHg at 25°C
• Refractive Index: n20/D 1.411(lit.)
• Storage Temp.: 2-8°C
• BRN: 2071361
• CAS DataBase Reference: ACETYLTRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETYLTRIMETHYLSILANE(13411-48-8)
• EPA Substance Registry System: ACETYLTRIMETHYLSILANE(13411-48-8)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 8-10-21
• TSCA: No
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 13411-48-8(Hazardous Substances Data)

Usage

General Description

Acetyltrimethylsilane is a chemical compound with the formula (CH3)3SiC(O)CH3. It is a derivative of silicon and is commonly used as a silylating agent in organic synthesis. As a silylating agent, acetyltrimethylsilane is used to protect functional groups and improve the volatility of organic compounds. It is also used as a reagent in the preparation of various silicon-containing compounds and in the synthesis of pharmaceuticals and agrochemicals. Additionally, acetyltrimethylsilane is used in the manufacturing of silicone-based polymers and as a reagent in the production of high-purity silicon.

InChI:InChI=1/C5H12OSi/c1-5(6)7(2,3)4/h1-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 109-92-2 ethyl vinyl ether 
• 13411-43-3 2-methyl-2-trimethylsilyl-1,3-dithiane 
• 2466-76-4 N-Acetylimidazole 
• 81177-92-6 ethyl 1-(trimethylsilyl)vinyl ether 
• 18000-27-6 trimethylsilyllithium 
• 75-36-5 acetyl chloride 
• 79678-01-6 1-methoxy-1-(trimethylsilyl)ethene 
• 201230-82-2 carbon monoxide 
• 1822-00-0 trimethylsilylmethyllithium 
• 80631-08-9 α-(trimethylsilyl)vinyl alcohol 

Downstream Products

• 120-72-9 indole 
• 116491-57-7 2-trimethylsilanyl-1H-indole 
• 846541-49-9 (Z)-3-trimethylsilyl-2-phenyl-2-butenoic acid 
• 147801-47-6 1-hydroxy-1-(4-fluorophenyl)-propan-2-one 
• 1228184-51-7 1-(3-benzyl-2-butyl-2,3-dihydrobenzo[d]oxazol-2-yl)-1,1-difluoro-2-(trimethylsilyl)propan-2-ol 
• 122-00-9 para-methylacetophenone 
• 941-98-0 1'-naphthacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 21860-07-1 methyl 3-acetylbenzoate 
• 53689-84-2 4-acetylbenzophenone 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 99-91-2 para-chloroacetophenone 
• 18992-80-8 1-(3-dimethylaminophenyl)-1-ethanone 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 

Relevant articles and documents

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Acetyldi-t-butylsilane and acetyldi-t-butylfluorosilane: Synthesis of functionalized acylsilanes

The preparation of acetyldi-t-butylsilane and acetyldi-t-butylfluorosilane, the first stable acylsilanes containing functional groups on silicon, is described. The new preparative procedure involves treatment of α-ethoxyvinyllithium with a halosilane to give an α-silyl enol ether, which is hydrolyzed under mild conditions to give the corresponding acetylsilane. Bulky t-butyl groups on silicon can be used to protect a reactive fluorine substituent during the hydrolysis step.

Acetyltrimethylsilane Keto-Enol System. Determination of the Keto-Enol Equilibrium Constant and Acid Dissociation Constants of the Keto and Enol Forms in Aqueous Solution

The enol isomer of the prototype α-silyl-substituted ketone, acetyltrimethylsilane, was generated by flash photolytic photooxidation of α-(trimethylsilyl)ethanol in aqueous solution and its rates of acid- and base-catalyzed ketonization in that medium were determined.These, in combination with rates of enolization of the ketone determined by iodine scavenging, provided the keto-enol equilibrium constant pK(E)=4.89, the dissociation constant of the enol ionizing as an oxygen acid pK(a)E=11.54, and the dissociation constant of the ketone ionizing as a carbon acid pK(a)K=16.44.Comparison of these results with corresponding values for simple alkyl-substituted carbonyl compounds shows that α-silyl substitution raised KE markedly, lowers K(a)E modestly, and raised K(a)K somewhat more strongly.Possible causes of these effects are discussed.

Reactions of Acyl Silanes with Fluoride Ion

Acyl silanes react with fluoride ion to give products arising either from intermediates equivalent to acyl anions or from rearrangement involving alkyl group migration from the silicon atom to the carbonyl carbon atom, depending upon acyl silane structure and reaction conditions.

Easy One-Step General Synthesis of Acylsilanes

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