59218-87-0 Usage
Description
TAS-F, or Tris(dimethylamino)sulfonium difluorotrimethylsilicate, is a versatile reagent widely used in organic synthesis. It serves as a source of fluoride ion for the synthesis of fluorinated compounds through C-F bond formation. TAS-F is also utilized in hydrosilylation, cyanomethylation of ketones, and Pd-catalyzed cross-coupling reactions. It is known for its mild deprotecting properties, making it suitable for the cleavage of silicon protecting groups and the synthesis of deoxyfluoro sugars.
Uses
Used in Organic Synthesis:
TAS-F is used as a source of fluoride ion for the synthesis of C-F compounds by nucleophilic displacement of sulfonates. It aids in the formation of C-F bonds, which are crucial in the development of various pharmaceuticals and agrochemicals.
Used in Fluorination of Hydroxyl-Containing Compounds:
TAS-F is used as a reagent for the fluorination of hydroxyl-containing compounds, which is an essential process in the production of certain pharmaceuticals and specialty chemicals.
Used in Hydrosilylation:
TAS-F is employed in hydrosilylation reactions, which involve the addition of a silicon-hydrogen bond to a carbon-carbon double bond, a process that is significant in the synthesis of various organic compounds.
Used in Cyanomethylation of Ketones:
TAS-F is used as a reagent in the cyanomethylation of ketones, a reaction that introduces a cyanomethyl group to a carbonyl compound, leading to the formation of cyanohydrins.
Used in Pd-Catalyzed Cross-Coupling Reactions:
TAS-F acts as an activator of vinylsilanes in Pd-catalyzed cross-coupling reactions, which are essential for the formation of carbon-carbon bonds in various organic compounds.
Used in Cleavage of Silicon Protecting Groups:
TAS-F is used as a mild deprotecting reagent for the cleavage of silicon protecting groups, which is vital in the synthesis of complex organic molecules where temporary protection of certain functional groups is necessary.
Used in Synthesis of Deoxyfluoro Sugars:
TAS-F is utilized in the synthesis of deoxyfluoro sugars by reacting with trifluoromethanesulfonyl derivatives of partially protected sugars, which are important in the development of bioactive compounds and pharmaceuticals.
Used in Stabilizing or Imparting High Nucleophilic Reactivity:
TAS-F serves as a source of sulfonium cation, which is capable of stabilizing or imparting high nucleophilic reactivity to other anions, enhancing the efficiency of various chemical reactions.
Used in Generation and Reactions of αand β-Halo Carbanions:
TAS-F is used for the generation and reactions of αand β-halo carbanions, which are key intermediates in organic synthesis, particularly in the formation of carbon-carbon bonds.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 59218-87-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,2,1 and 8 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 59218-87:
(7*5)+(6*9)+(5*2)+(4*1)+(3*8)+(2*8)+(1*7)=150
150 % 10 = 0
So 59218-87-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H18N3S/c1-7(2)10(8(3)4)9(5)6/h1-6H3/q+1
