5908-40-7

Basic information

• Product Name: N~2~-(phenylacetyl)-N-(4-phenyl-1,3-thiazol-2-yl)-N~2~-propylglycinamide
• Synonyms: (Trimethylsilyl)acetone;1-(Trimethylsilyl)-2-propanone;2-Propanone, 1-(trimethylsilyl)-;Methyl (trimethylsilyl)methyl ketone
• CAS NO: 5908-40-7
• Molecular Formula: C₆H₁₄OSi
• Molecular Weight: 393.5019
• Mol File: 5908-40-7.mol
• Article Data: 2

Chemical Properties

• Density: 1.236g/cm³
• Refractive Index: 1.628
• CAS DataBase Reference: N~2~-(phenylacetyl)-N-(4-phenyl-1,3-thiazol-2-yl)-N~2~-propylglycinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N~2~-(phenylacetyl)-N-(4-phenyl-1,3-thiazol-2-yl)-N~2~-propylglycinamide(5908-40-7)
• EPA Substance Registry System: N~2~-(phenylacetyl)-N-(4-phenyl-1,3-thiazol-2-yl)-N~2~-propylglycinamide(5908-40-7)

Safety Data

• Hazardous Substances Data: 5908-40-7(Hazardous Substances Data)

Usage

Physical properties

Clear liquid; bp 74 °C/96 mmHg; d 0.8274 g cm?3 (26 °C), n26/D 1.4188.

Uses

Trimethylsilylacetone reacts with Grignard or organolithium reagents to provide, after elimination, 2-substituted 2-propenes; in combination with fluoride ion, gives chemistry of the corresponding enolate ion; can direct electrophilic substitution to either side of the carbonyl group, participating in (but not limited to) reactions: Preparation of 2-substituted α-Alkenes, Reaction with Electrophiles, Reaction with Fluoride Ion, Reaction with Strong Bases, etc.

Preparation

The best procedure for the preparation of trimethylsilylacetone is the reaction of trimethylsilylmethylmagnesium chloride or bromide with acetic anhydride.5 Other useful preparative methods for α-trimethylsilyl ketones involve the reaction of trimethylsilylmethylmagnesium chloride with acid chlorides,6 or with aldehydes followed by oxidation of the resulting β-hydroxysilane to the ketone.2e When the trialkylsilyl group is very large, particularly the triisopropylsilyl group, a rearrangement from the silyl enol ether to the α-silyl ketone is possible.

Upstream product

• 18243-38-4 (trimethylsilyl)methylmagnesium bromide 
• 38860-07-0 1,1-Bis(trimethylsilyl)aceton 
• 19061-00-8 bis(trimethylsilyl)ketene 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 75-36-5 acetyl chloride 
• 128164-34-1 1-amino-2-(trimethylsilyl)-2-propanol 
• 108-24-7 acetic anhydride 
• 38860-08-1 2-(trimethylsiloxy)-1-(trimethylsilyl)propene 

Downstream Products

• 1825-62-3 ethyl trimethylsilyl ether 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 213250-62-5 methyl-2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)-4-methylenecyclohexylidene)acetate 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 37166-20-4 2-phenyl-1-(trimethylsilyl)propan-2-ol 

Relevant articles and documents

Acetylsilane O-Silylcyanohydrins as Precursors to α-Silyl Ketones and β-Siloxy-N,N-bissilylenamines

Reduction of acetylsilane O-silylcyanohydrins gave β-amino-α-hydroxysilanes, which were diazotized to give α-silyl ketones.The addition of organolithium reagents to the cyanohydrins was accompanied by sequential C -> N and O -> N silyl group migrations.Silylation of the resulting lithium enolates afforded β-siloxy-N,N-bissilylenamines.