Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester
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Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester
structure -
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CAS No:
69739-34-0
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Formula:
C7H15F3O3SSi
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Chemical Name:
Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester
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Synonyms:
Methanesulfonic acid, trifluoro-, (1,1-dimethylethyl)dimethylsilyl ester;t-Butyldimethylsilyl triflate;t-butyldimethylsilyltrifluormethansulfonate;t-Butylmethylsilyl triflate;TBDMS triflate, Trifluoromethanesulfonic acid tert-butyldimethylsilylester;SILANE TBM2 TRIFLATE;T-BUTYLDIMETHYLSILYL TRIFLUOROMETHANESULFONATE;Silane TBM2 triflate, TBDMS triflate, Trifluoromethanesulfonic acid tert-butyldimethylsilylester
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CAS No:
Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester Basic Attributes
264.34
264.34
2370068
274-102-0
No
DTXSID50220034
Clear colorless to yellow
29310095
Characteristics
bp 60°C/7 mmHg; colorless oil, d 1.151 g cm3. Solubility: sol most organic solvents such as pentane, CH2Cl2, etc.
1.151 g/mL at 25 °C(lit.)
<0°C
65-67 °C12 mm Hg(lit.)
n20/D1.385(lit.)
DECOMPOSES
2-8°C
Safety Information
III
3
3
C,F
26-36/37/39-45-25-16
10-34-37
UN 2920 8/PG 2
|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 56 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester Use and Manufacturing
TrifluoroMethanesulfonic acid tert-butyldiMethylsilyl ester is a highly reactive silylating agent and lewis acid capable of converting primary, secondary and tertiary alcohols to their respectctive TBDMS. TrifluoroMethanesulfonic acid tert-butyldiMethylsilyl ester is also used to covert ketones and lactones into their enol silyl ethers.
t-Butyldimethylsilyl Trifluoromethanesulfonate is used as a highly reactive silylating agent and Lewis acid capable of converting primary, secondary, and tertiary alcohols1b to the corresponding TBDMS ethers, and converting ketones and lactones, into their enol silyl ethers; promoting conjugate addition of alkynylzinc compounds and triphenylphosphine5 to α,β-enones; activation of chromones in [4 + 2] cycloaddition reactions;rearrangement of allylic tributylstannyl silyl ethers; activation of pyridine rings toward Grignard reagents and transalkylation of tertiary amine N-oxides;and transformation of N-t-butoxycarbonyl groups into N-alkoxycarbonyl groups.
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.
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