82113-66-4

Basic information

• Product Name: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE
• Synonyms: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE;[Bis(trifluoromethanesulfonyl)amino]trimethylsilane;TMS Triflimide;[Bis(trifluoromethanesulfonyl)amino]trimethylsilane TMS Triflimide;1,1,1-trifluoro-N-(trifluoroMethylsulfonyl)-N-(triMethylsilyl)MethanesulfonaMide;Methanesulfonamide,1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]-N-(trimethylsilyl)-;N-(Trimethylsilyl)bis(trifluoromethanesulfonyl)imide
• CAS NO: 82113-66-4
• Molecular Formula: C₅H₉F₆NO₄S₂Si
• Molecular Weight: 353.34
• Product Categories: Si (Classes of Silicon Compounds);Si-N Compounds;Trimethylsilylazide, etc.
• Mol File: 82113-66-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 115 °C / 2mmHg
• Flash Point: 97.1°C
• Appearance: /
• Density: 1.543g/cm³
• Vapor Pressure: 0.046mmHg at 25°C
• Refractive Index: 1.405
• Storage Temp.: Freezer
• Solubility: soluble in most common organic solvents, commonly used in dichloromethane, toluene, diethyl ether.
• PKA: -26.49±0.70(Predicted)
• CAS DataBase Reference: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE(82113-66-4)
• EPA Substance Registry System: N-(TRIMETHYLSILYL)BIS(TRIFLUOROMETHANESULFONYL)IMIDE(82113-66-4)

Safety Data

• Hazardous Substances Data: 82113-66-4(Hazardous Substances Data)

Usage

Physical properties

colorless liquid, bp: 115°C(2 Torr).

Uses

Methanesulfonamide, 1,1,1-Trifluoro- N[(trifluoromethyl)sulfonyl]- N(trimethylsilyl)-? can be used as Lewis acid catalyst for a variety of organic transformations.

Preparation

It is easily prepared in situ through protodesilation by mixing commercially available allyltrimethylsilane (or any TMS enol ether) and Tf2NH. Originally prepared by mixing Tf2NH with trimethylsilane at low temperature or mixing AgNTf2 with TMSCl.

InChI:InChI=1/C5H9F6NO4S2Si/c1-19(2,3)12(17(13,14)4(6,7)8)18(15,16)5(9,10)11/h1-3H3

Upstream product

• 18292-38-1 2-methallyltrimethylsilane 
• 82113-65-3 bis(trifluoromethanesulfonyl)amide 
• 1036000-94-8 di-tert-butyl(1,1'-biphenyl)-2-ylphosphinegold(I) bis(trifluoromethanesulfonimidate) 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 762-72-1 allyl-trimethyl-silane 
• 75-77-4 chloro-trimethyl-silane 
• 189114-61-2 silver(I) triflimide 

Relevant articles and documents

User friendly synthesis of VogelS silyl sulfinate and its application in quantitative Gc-Ms analysis

The synthesis of trimethylsilyl 2-methylprop-2-ene-1-sulfinate (Vogel's silyl sulfinate) from methallyltrimethylsilane and SO2 in the presence of Tf2NTMS was developed. The title compound silylates carbohydrates and other polyhydroxylated compounds by producing SO2 and isobutene as gaseous side products. This silylation procedure is perfectly suitable for derivatization and subsequent GC-MS quantitative analysis of ribose and malic acid as representatives of organic polyhydroxylated compounds.

A triple-aldol cascade reaction for the rapid assembly of polyketides

(Figure Presented) Triple play: The title reaction of 1 with simple aldehydes gives 3,5,7-trisilyloxy aldehydes in high yields and diastereoselectivities with extremely low catalyst loading (see scheme). lodobenzene facil-itates the third aldol reaction by apparently acting as a Lewis base towards the silyl catalyst. Tf=trifluoromethanesulfonyl.