CAS 69739-34-0: (1,1-Dimethylethyl)dimethylsilyl 1,1,1-trifluoromethanesulfonate

S03375 - tert-Butyldimethylsilyl trifluoromethanesulphonate

t-Butyldimethylsilyl trifluoromethanesulfonate, 98%

tert-Butyldimethylsilyl trifluoromethanesulfonate is involved in the introduction of a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane used in Cope rearrangement. It is associated with a thiolane and promotes the chalcogenide-Morita-Baylis-Hillman reaction. Further, it is used as a highly reactive silylating agent. In addition to this, it is used to prepare enol silyl ethers by reacting with ketones and lactones. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

tert-Butyldimethylsilyl trifluoromethanesulphonate

Stability Moisture Sensitive Applications Tert-Butyldimethylsilyl Trifluoromethanesulfonate is a highly reactive silylating agent and lewis acid capable of converting primary, secondary and tertiary alcohols to their respectctive TBDMS. Tert-Butyldimethylsilyl Trifluoromethanesulfonate is also used to covert ketones and lactones into their enol silyl ethers. Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package References Hua, D.H. et al.: e-ROS Encyc. Reag. Org. Synth., No pp. given (2001); Suzuki, T. et al.: Synthesis, 4, 555 (2001);

Trialkylsilyl Blocking Agent Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure. tert-Butyldimethylsilyltrifluoromethanesulfonate; TBS-OTf; t-Butyldimethylsilyltriflate More reactive than SIB1935.0Converts acetates to TBS ethersUsed for the protection of alcohols, amines, thiols, lactams, and carboxylic acidsClean NMR characteristics of protecting groupFacile removal with flouride ion sourcesSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure

tert-Butyldimethylsilyl trifluoromethanesulfonate is a nucleophilic reagent that forms an addition product with metal carbonyls. It can be used for the synthesis of indacaterol maleate, which is a phosphite prodrug for the treatment of asthma and chronic obstructive pulmonary disease. Tert-butyldimethylsilyl trifluoromethanesulfonate has been shown to catalyze asymmetric hydrogenation reactions in the presence of ammonia as a chiral auxiliary. This reagent has also been shown to inhibit the growth of bacteria and fungi through its ability to inhibit protein synthesis.

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.