64035-64-9

Basic information

• Product Name: (TRIMETHYLSILYL)METHYL TRIFLUOROMETHANESULFONATE
• Synonyms: TRIFLUOROMETHANESULFONIC ACID (TRIMETHYLSILYL)METHYL ESTER;TRIMETHYLSILYLMETHYL TRIFLATE;(TRIMETHYLSILYL)METHYL TRIFLUOROMETHANESULFONATE;trimethylsilylmethylatingreagent;Trimethylsiylmethyltrifluoromethanesulfnate;(Trimethylsilyl)methyl Trifluoromethanesulfonate [Trimethylsilylmethylating Reagent];(TRIMETHYLSILYL)METHYL TRIFLUOROMETHANESULFONATE, 95+%;Trifluoromethanesulfonic Acid (Trimethylsilyl)methyl Ester (Trimethylsilyl)methyl Triflate
• CAS NO: 64035-64-9
• Molecular Formula: C₅H₁₁F₃O₃SSi
• Molecular Weight: 236.28
• Product Categories: Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 64035-64-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 49-51 °C9 mm Hg(lit.)
• Flash Point: 119 °F
• Appearance: clear yellow-orange liquid
• Density: 1.182 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.1mmHg at 25°C
• Refractive Index: n20/D 1.376(lit.)
• Storage Temp.: 2-8°C
• BRN: 2365813
• CAS DataBase Reference: (TRIMETHYLSILYL)METHYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: (TRIMETHYLSILYL)METHYL TRIFLUOROMETHANESULFONATE(64035-64-9)
• EPA Substance Registry System: (TRIMETHYLSILYL)METHYL TRIFLUOROMETHANESULFONATE(64035-64-9)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-28-36/37/39-45-16
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 8-10-21
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 64035-64-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H11F3O3SSi/c1-13(2,3)4-11-12(9,10)5(6,7)8/h4H2,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 3219-63-4 (trimethylsilyl)methanol 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 113638-06-5 4,4,5,5-Tetrakis-(4-chloro-phenyl)-[1,3]dithiolane 
• 103852-58-0 <1-(phenylthio)ethylidene>-1-(trimethylsilyl)methylamine 

Relevant articles and documents

Preparation of (Trimethylsilyl)methyl Halides and Trifluoromethanesulfonate by Methylene Insertion Using Diazomethane

(Trimethylsilyl)methyl halides (1,3) and trifluoromethanesulfonate (triflate) (2) were prepared by inserting a methylene group into the silicon-heteroatom bond of trimethylsilyl halides and triflate using diazomethane.

Dienophilic Properties of Phenyl Vinyl Sulfone and trans-1-(Phenylsulfonyl)-2-(trimethylsilyl)ethylene. Their Utilization as Synthons for Ethylene, 1-Alkenes, Acetylene, and Monosubstituted Alkynes in the Construction of Functionalized Six-Membered Rings via ? Cycloaddition Meth.

Useful procedures for effecting the indirect capture of ethylene, acetylene, 1-alkenes, and monosubstituted alkynes in Diels-Alder cycloadditions have been developed.In the first sequence, phenyl vinyl sulfone is shown to enter into ? reactions as a moderately reactive dienophile and to do so with very good regioselectivity.The resulting adducts can be directly desulfonated or alkylated prior to such reduction.A wide range of functional groups can be appended in this fashion at a specific locus within the newly formed six-membered ring.When the analogous chemistry is applied to trans-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene (2), adducts result which undergo ready fluoride ion induced elimination with efficient introduction of a double bond.The use of 2 and its d2 derivative is highlighted by the synthesis of several functionalized dibenzobarrelenes.