TAS-F Chemical Properties

storage temp. 

2-8°C

solubility 

R = Me, sol MeCN, pyridine, benzonitrile; partially sol THF. R = Et, sol THF, MeCN. Both react slowly with MeCN.

form 

powder

color 

White to off-white

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

3577020

Safety Information

Hazard Codes 

C

Risk Statements 

14-34-37

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

3-10-21

Hazard Note 

Corrosive/Moisture Sensitive

TSCA 

No

HazardClass 

8

PackingGroup 

II

HS Code 

2931900090

MSDS

• Language:English Provider:SigmaAldrich

TAS-F Usage And Synthesis

Physical properties

R = Me, mp 98–101 °C; R = Et, mp 90–95 °C.

Uses

Tris(dimethylamino)sulfonium Difluorotrimethylsilicate is used in anhydrous fluoride ion source; synthesis of C–F compounds by nucleophilic displacement of sulfonates;promoter for electrophilic reactions of silyl enolates of ketones and esters; source of sulfonium cation capable of stabilizing or imparting high nucleophilic reactivity to other anions; activator of vinylsilanes in Pd-catalyzed cross-coupling reactions; also used for generation8 and reactions of α- and β-halo carbanions; hydrosilylation and cyanomethylation of ketones.

Uses

Tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF₂SiMe₃) can be used as a mild deprotecting reagent for the cleavage of silicon protecting groups.
It can also be used

• To synthesize deoxyfluoro sugars by reacting with trifluoromethanesulfonyl derivatives of partially protected sugars.
• As a reagent for the fluorination of hydroxyl-containing compounds.

Preparation

The methyl derivative is prepared by the reaction of dimethylaminotrimethylsilane and sulfur tetra- fluoride at ?70°C to rt in ether; the precipitated solid is filtered off.1a The ethyl derivative is best prepared by the reaction of N,N-diethylaminosulfur trifluoride (DAST) and diethylaminotrimethylsilane.

General Description

Tris(dimethylamino)sulfonium difluorotrimethylsilicate is widely used in organic synthesis as a source of fluoride ion for the synthesis of fluorinated compounds by C-F bond formation. It is also used as a reagent in hydrosilylation, cyanomethylation of ketones and Pd-catalyzed cross-coupling reactions.

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