13257-81-3

Basic information

• Product Name: 4-TRIMETHYLSILOXY-3-PENTEN-2-ONE
• Synonyms: 4-(Trimethylsilyloxy)-3-pentene-2-one;(E)-4-((triMethylsilyl)oxy)pent-3-en-2-one;TMSACAC;4-[(trimethylsilyl)oxy]-3-penten-2-on;2-TRIMETHYLSILOXYPENT-2-EN-4-ONE;2-TRIMETHYLSILOXYPENT-2-ENE-4-ONE;ACETYLACETONE ENOL TRIMETHYLSILYL ETHER;4-TRIMETHYLSILOXY-3-PENTEN-2-ONE
• CAS NO: 13257-81-3
• Molecular Formula: C₈H₁₆O₂Si
• Molecular Weight: 172.3
• EINECS: 236-252-5
• Product Categories: Monoalkoxysilanes;Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Si-O Compounds;Synthetic Organic Chemistry
• Mol File: 13257-81-3.mol

Chemical Properties

• Boiling Point: 66-68 °C4 mm Hg(lit.)
• Flash Point: 58°C
• Appearance: /
• Density: 0.912 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.255mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: 2-8°C
• BRN: 1759078
• CAS DataBase Reference: 4-TRIMETHYLSILOXY-3-PENTEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TRIMETHYLSILOXY-3-PENTEN-2-ONE(13257-81-3)
• EPA Substance Registry System: 4-TRIMETHYLSILOXY-3-PENTEN-2-ONE(13257-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 13257-81-3(Hazardous Substances Data)

Usage

Uses

Used in Research Laboratories:
4-Trimethylsiloxypentan-3-one is used as a chemical intermediate for the synthesis of other organosilicon compounds and in various chemical reactions. Its stability and reactivity make it a valuable tool in the development of new materials and compounds.
Used in Material Science:
4-Trimethylsiloxypentan-3-one is used as a precursor in the development of new materials with potential applications in various industries, such as electronics, automotive, and aerospace. 4-TRIMETHYLSILOXY-3-PENTEN-2-ONE's unique structure and properties can contribute to the creation of innovative materials with improved performance characteristics.
Used in Pharmaceutical Research:
4-Trimethylsiloxypentan-3-one is used as a building block in the synthesis of new drug candidates, particularly in the field of organosilicon chemistry. Its unique structure may offer novel therapeutic opportunities and contribute to the discovery of new pharmaceutical agents.
Used in Chemical Synthesis:
4-Trimethylsiloxypentan-3-one is used as a reagent in the synthesis of complex organic molecules, including natural products and potential bioactive compounds. Its versatility in chemical reactions allows for the exploration of new synthetic pathways and the development of more efficient synthetic methods.

InChI:InChI=1/C8H16O2Si/c1-7(9)6-8(2)10-11(3,4)5/h6H,1-5H3/b8-6+

Upstream product

• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 123-54-6 acetylacetone 
• 400-53-3 trimethylsilyl trifluoroacetate 
• 105532-86-3 N,O-bis(trimethylsilyl)-N-methoxycarbamate 
• 10416-58-7 N,N-bis(trimethylsilyl)acetamide 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 19159-25-2 sucrose octakis(trimethylsilyl) ether 
• 1221016-29-0 1-hydroxy-1-phenyl-5-(trimethylsilyloxy)hex-4-en-3-one 
• 106915-02-0 3-(cyclohex-2-en-1-yl)pentane-2,4-dione 
• 1613703-91-5 1-[4-(4-methoxyphenyl)-2-methyl-5-(3-methylbut-2-en-2-yl)-furan-3-yl]ethanone 
• 1021178-48-2 methyl 3-chloro-2-hydroxy-4,6-dimethylbenzoate 
• 1190220-05-3 2-(4-chlorophenylsulfanyl)-3,4,6-trimethyl-benzoic acid methyl ester 
• 1190220-02-0 2-(4-ethylphenylsulfanyl)-3,4,6-trimethyl-benzoic acid methyl ester 
• 1190220-01-9 2-(4-ethylphenylsulfanyl)-4,6-dimethyl-benzoic acid methyl ester 
• 1190220-08-6 2-(4-fluorophenylsulfanyl)-3,4,6-trimethylbenzoic acid methyl ester 
• 1190219-99-8 3,4,6-trimethyl-2-(4-tolylsulfanyl)benzoic acid methyl ester 
• 1190220-06-4 2-(3-chlorophenylsulfanyl)-4,6-dimethyl-benzoic acid methyl ester 
• 1190220-07-5 2-(4-fluorophenylsulfanyl)-4,6-dimethyl-benzoic acid methyl ester 
• 1190220-00-8 2,4-dimethyl-6-(m-tolylsulfanyl)benzoic acid methyl ester 
• 1190220-04-2 3-chloro-6-(4-chlorophenylsulfanyl)-2,4-dimethyl-benzoic acid methyl ester 

Relevant articles and documents

A CLASS OF NEW SILYLATING AGENTS. II. A HIGHLY REACTIVE REAGENT FOR INTRODUCTION OF THE TRIMETHYLSILYL GROUP.

Trimethylsilyl enol ethers of pentane-2,4-dione and methyl acetoacetate react rapidly with alcohols at room temperature without the need catalytic for assistance to give high isolated yields of trimethylsilyl ethers.

Alkyloximes and imines via silyl carbamates

The reactions between different N,O-bis-trimethylsilyl-carbamates and oxo compounds were studied. The N,O-bis-trimethylsilyl-N-methoxy-carbamate converts ketones to the corresponding O-methyl oximes. The product is usually a mixture of syn and anti isomers. If the carbonyl compound bears a hydroxyl group, the oxime formation and the O-silylation take place simultaneously. In the case of -haloketones, the undesired substitution of halogen was not observed. The reactions between N,O-bis-trimethylsilyl-N-methyl-carbamate and oxo compounds resulted in the corresponding imines, although the yield are moderate in some cases. Analoguos reaction of ferrocenylated oxo derivatives gave similar results.

Studies towards the synthesis of (+)-ptilomycalin A; stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams

Highly stereoselective N-acyliminium ion coupling reactions of β-ketoester derived silyl enol ethers with enantiopure lactams derived from (S)-malic acid are reported. This reaction type is applied in the synthesis of the enantiopure C-2 substituted lactam 27, a plausible intermediate in a projected synthesis of ptilomycalin A.

Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones

Lewis acids are employed as catalysts in the annulation of 1,4- and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) end ethers of β-diketones and β-keto esters. A variety of 2-(alkoxycarbonyl)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regiocontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation reaction.

Ring-fluorinated pyrazoles

2-Fluoro-1,3-diketones react with phenylhydrazine to yield ring-fluorinated pyrazoles in high yield.An isoxazole is produced when 2-fluoro-1,3-diphenyl-1,3-propandione is treated with hydroxylamine hydrochloride,

ETUDE DANS LA SERIE DES ORGANOSILYLAZOLES. II. REACTION D'ADDITION NUCLEOPHILE SUR LES DERIVES CARBONYLES

The reactivity of organosilicon amines of imidazole, 1,2,4-triazole and benzotriazole towards aldehydes and ketones has been studied.Aldehydes react easily and give the addition products at room temperature.With ketones, the reactions depend both on the organosilicon amine and the ketone used.With trimethylsilyl-1 imidazole, ketones having an enolic form stabilized by conjugation, form enoxysilanes.