TAS-F
Synonym(s):TASF;TAS-F;Tris(dimethylamino)sulfur trimethylsilyl difluoride
- CAS NO.:59218-87-0
- Empirical Formula: C9H24F2N3SSi
- Molecular Weight: 272.45
- MDL number: MFCD00012170
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-04-23 13:52:06
What is TAS-F?
Physical properties
R = Me, mp 98–101 °C; R = Et, mp 90–95 °C.
The Uses of TAS-F
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.
The Uses of TAS-F
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.
Properties of TAS-F
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. |
color | White to off-white |
Sensitive | Moisture Sensitive |
Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
BRN | 3577020 |
Safety information for TAS-F
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 |
GHS Hazard Statements |
H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P260:Do not breathe dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for TAS-F
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