ChemicalBook CAS DataBase List 59218-87-0

59218-87-0

Name	TAS-F
CAS	59218-87-0
EINECS(EC#)	218-362-5
Molecular Formula	C9H24F2N3SSi
MDL Number	MFCD00012170
Molecular Weight	272.45
MOL File	59218-87-0.mol

Synonyms

TAS-F Tris(dimethylamino)sulfonium tris(dimethylamino)sulfanium Tris(dimethylamino)(trimethylsilyl)sulfur TRIS(DIMETHYLAMINO)SULFUR TRIMETHYLSILY DIFLUORIDE TRIS(DIMETHYLAMINO)SULFUR (TRIMETHYLSILYL)DIFLUORIDE TRIS(DIMETHYLAMINO)(TRIMETHYLSILYL)SULFUR DIFLUORIDE TRIS(DIMETHYLAMINO)(TRIMETHYLSILYL)SULPHUR DIFLUORIDE Tris(dimethylamino)sulfonium trimethylsilyldifluoride TRIS(DIMETHYLAMINO)SULFONIUM DIFLUOROTRIMETHYLSILICATE TRIS(DIMETHYLAMINO)SULFUR(TRIMETHYLSILYL)DIFLUORIDE 95% ifluoro(trimethyl)silanuide,tris(dimethylamino)sulfanium difluoro(trimethyl)silanuide,tris(dimethylamino)sulfanium Tris(dimethylamino)sulfonium difluorotrimethylsilicate(IV) Tris(dimethylamino)(trimethylsilyl)sulphur difluoride, tech Tris(dimethylamino)sulphur trimethylsilyl difluoride, TAS-F TRIS(DIMETHYLAMINO)SULFUR(TRIMETHYLSILYL)DIFLUORIDE, tech-95 TRIS(DIMETHYLAMINO)SULFUR (TRIMETHYLSILYL)DIFLUORIDE, PRACT. TRIS(DIMETHYLAMINO)SULFUR (TRIMETHYL-SIL YL)DIFLUORIDE, TECH. Tris(dimethylamino)sulphonium difluoro(trimethyl)silicate, tech TAS-F, TASF, Tris(dimethylamino)sulfur trimethylsilyl difluoride Tris(diMethylaMino)sulfoniuM difluorotriMethylsilicate technical grade Sulfiliminium, S,S-bis(dimethylamino)-N,N-dimethyl-, difluorotrimethylsilicate(1-)

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
InChI	1S/C6H18N3S.C3H9F2Si/c1-7(2)10(8(3)4)9(5)6;1-6(2,3,4)5/h1-6H3;1-3H3/q+1;-1
InChIKey	JMGVTLYEFSBAGJ-UHFFFAOYSA-N
SMILES	C[Si-](C)(C)(F)F.CN(C)[S+](N(C)C)N(C)C

Safety Data

Symbol(GHS)	GHS05
Signal word	Danger
Hazard statements	H314
Precautionary statements	P260-P280-P301+P330+P331-P303+P361+P353-P305+P351+P338
Hazard Codes	C
Risk Statements	14-34-37 less more
Safety Statements	26-36/37/39-45 less more
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
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Skin Corr. 1B

Hazard Information

Physical properties

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

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.

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.

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.

reaction suitability

reagent type: reductant

Spectrum Detail

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