6651-34-9

Basic information

• Product Name: 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE
• Synonyms: 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE;2-METHYL-1-(TRIMETHYLSILYLOXY)-1-PROPENE;isobutyraldehyde trimethylsilyl enol ether;Itse;Silane, trimethyl((2-methyl-1-propenyl)oxy)-;Trimethyl((2-methylprop-1-en-1-yl)oxy)silane;2-Methyl-1-(trimethylsilyloxy)-1-propene 99%
• CAS NO: 6651-34-9
• Molecular Formula: C₇H₁₆OSi
• Molecular Weight: 144.29
• Product Categories: Enol Ethers;Organic Building Blocks;Oxygen Compounds;Building Blocks;Chemical Synthesis;Enol Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 6651-34-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 114-116 °C650 mm Hg(lit.)
• Flash Point: 57 °F
• Appearance: /
• Density: 0.785 g/mL at 25 °C(lit.)
• Vapor Pressure: 19.2mmHg at 25°C
• Refractive Index: n20/D 1.409(lit.)
• CAS DataBase Reference: 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE(6651-34-9)
• EPA Substance Registry System: 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE(6651-34-9)

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
• TSCA: No
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 6651-34-9(Hazardous Substances Data)

Usage

Description

2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE is an organosilicon compound characterized by the presence of a trimethylsilyl ether group attached to a 2-methyl-1-propene backbone. This unique structure endows it with specific chemical properties that make it a versatile reagent in various organic synthesis processes.

Uses

Used in Organic Synthesis:
2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE is used as a nucleophile in Lewis Acid-Catalyzed reactions for its ability to participate in the formation of new chemical bonds under the influence of a Lewis acid catalyst. This application is particularly valuable in the synthesis of complex organic molecules where selective bond formation is required.
Used in Pharmaceutical and Biochemical Research:
In the field of pharmaceutical and biochemical research, 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE may be used as a reagent in the direct conversion of α-amino acids into β-amino aldehydes. This transformation is significant as it allows for the synthesis of biologically active compounds and intermediates that are otherwise challenging to obtain, facilitating the development of new drugs and therapeutic agents.

InChI:InChI=1/C7H16OSi/c1-7(2)6-8-9(3,4)5/h6H,1-5H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 56640-70-1 2-methylprop-1-en-1-ol 
• 78-84-2 isobutyraldehyde 
• 18881-60-2 bis-trimethylsilanyl-acetonitrile 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 15693-82-0 (trimethylsilyl)cobalt tetracarbonyl 

Downstream Products

• 54322-96-2 (+/-)-3-Hydroxy-2,2-dimethyl-5-phenylvaleraldehyde 
• 53282-30-7 trifluoro-methanesulfonic acid 2-methyl-propenyl ester 
• 54322-95-1 3-Hydroxy-2,2-dimethyl-4-phenyl-butyraldehyde 
• 55638-19-2 3-Chloro-benzoic acid 2-hydroxy-2-methyl-1-trimethylsilanyloxy-propyl ester 
• 142916-45-8 1-(2,2-dimethyl-3-oxopropyl)perhydro-2-azepinone 
• 132151-45-2 2,2-dimethyl-6-p-tolylthiohexane-1,5-dione 
• 132177-89-0 2,2-dimethyl-5-methoxy-6-p-tolylhex-4-en-1-one 
• 132151-59-8 2,4-di-p-tolylthiobutan-3-onyl chloride 
• 128672-53-7 2,2-dimethyl-3-methoxy-4-p-tolylthiopent-4-enal 
• 128672-56-0 E-2,2-dimethyl-5-methoxy-4-p-tolylthiopent-4-enal 
• 128672-55-9 Z-2,2-dimethyl-5-methoxy-4-p-tolylthiopent-4-enal 
• 20967-51-5 3-(phenylthio)-2,2-dimethylpropanal 
• 420-56-4 trimethylsilyl fluoride 
• 84224-50-0 (2-Methyl-1-propenyl)-methansulfonat 

Relevant articles and documents

Sc(OTf)3-catalyzed smooth tandem [3+2] cycloaddition/ring opening of donor-acceptor cyclopropane 1,1-diesters with enol silyl ethers

Catalyzed by Lewis acids, donor-acceptor cyclopropane 1,1-diesters reacted with enol silyl ethers to afford 1,6-dicarbonyl compounds in moderate to excellent yields. This supplied a mild carbon-carbon bond-forming method from the ring opening of cyclopropanes. A smooth tandem [3+2] cycloaddition/ring opening process has been clearly proved by an independent experiment.

Scope and limitations of the [1,2]-alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans

Acid catalysed rearrangement of a series of 4-RS-1,3-diols (R = Me, Et, Bn and H) with toluene-p-sulfonic acid in dichloromethane gives stereospecifically substituted tetrahydrofurans via a [1,2]-SR shift in near quantitative yield. We comment on the structural variation of the migrating (RS) substituent and that of the migration origin and terminus on the outcome of the title reaction. We also report on the surprising similarity between an alkylsulfanyl (RS) and sulfanyl (SH) migrating group.