|
Product Name: | TAS-F | Synonyms: | TRIS(DIMETHYLAMINO)SULFUR(TRIMETHYLSILYL)DIFLUORIDE, tech-95;Tris(dimethylamino)sulphonium difluoro(trimethyl)silicate, tech;Tris(dimethylamino)sulphur trimethylsilyl difluoride, TAS-F;Tris(diMethylaMino)sulfoniuM difluorotriMethylsilicate technical grade;TRIS(DIMETHYLAMINO)SULFUR (TRIMETHYLSILYL)DIFLUORIDE, PRACT.;TAS-F, TASF, Tris(dimethylamino)sulfur trimethylsilyl difluoride;Tris(dimethylamino)sulfonium;Tris(dimethylamino)sulfonium trimethylsilyldifluoride | CAS: | 59218-87-0 | MF: | C9H24F2N3SSi | MW: | 272.45 | EINECS: | | Product Categories: | | Mol File: | 59218-87-0.mol | |
| 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 | Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents | Sensitive | Moisture Sensitive | BRN | 3577020 |
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 |
| 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. |
| TAS-F Preparation Products And Raw materials |
|