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| Product Name: | TAS-F | | Synonyms: | TRIS(DIMETHYLAMINO)SULFUR(TRIMETHYLSILYL)DIFLUORIDE 95%;Tris(dimethylamino)(trimethylsilyl)sulfur;Sulfiliminium, S,S-bis(dimethylamino)-N,N-dimethyl-, difluorotrimethylsilicate(1-);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. | | 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 | | Sensitive | Moisture Sensitive | | Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents | | 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 |
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