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| | Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester Basic information |
| Product Name: | Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester | | Synonyms: | Methanesulfonic acid, trifluoro-, (1,1-dimethylethyl)dimethylsilyl ester;t-butyldimethylsilyltrifluormethansulfonate;t-Butylmethylsilyl triflate;TBDMS triflate, Trifluoromethanesulfonic acid tert-butyldimethylsilylester;SILANE TBM2 TRIFLATE;Silane TBM2 triflate, TBDMS triflate, Trifluoromethanesulfonic acid tert-butyldimethylsilylester;(R)-4-isopropyl-5,5-diphenyloxazolidine-2-thione;Methanesulfonic acid, trifluoro-, (1,1-diMethylethyl)diMethylsilyl ester (9CI) | | CAS: | 69739-34-0 | | MF: | C7H15F3O3SSi | | MW: | 264.34 | | EINECS: | 274-102-0 | | Product Categories: | metal triflate compounds;Biochemistry;Protection & Derivatization Reagents (for Synthesis);Reagents for Oligosaccharide Synthesis;Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Silyl Esters;Si-O Compounds;Synthetic Organic Chemistry | | Mol File: | 69739-34-0.mol |  |
| | Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester Chemical Properties |
| Melting point | <0°C | | Boiling point | 65-67 °C12 mm Hg(lit.) | | density | 1.151 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.385(lit.) | | Fp | 98 °F | | storage temp. | 2-8°C | | solubility | Slightly miscible with chloroform. | | form | Fuming Liquid | | Specific Gravity | 1.151 | | color | Clear colorless to yellow | | Water Solubility | DECOMPOSES | | Sensitive | Moisture Sensitive | | Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents | | BRN | 2370068 | | Stability: | Moisture Sensitive | | InChIKey | WLLIXJBWWFGEHT-UHFFFAOYSA-N | | CAS DataBase Reference | 69739-34-0(CAS DataBase Reference) | | NIST Chemistry Reference | Tert-butyldimethylsilyl trifluoromethanesulfonate(69739-34-0) |
| Hazard Codes | C,F | | Risk Statements | 10-34-37 | | Safety Statements | 26-36/37/39-45-25-16 | | RIDADR | UN 2920 8/PG 2 | | WGK Germany | 3 | | F | 10-21 | | Hazard Note | Flammable/Corrosive | | TSCA | No | | HazardClass | 3 | | PackingGroup | III | | HS Code | 29310095 |
| | Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester Usage And Synthesis |
| Chemical Properties | clear colorless to yellow fuming liquid | | Physical properties | bp 60°C/7 mmHg; colorless oil, d 1.151 g cm?3.
Solubility: sol most organic solvents such as pentane, CH2Cl2,
etc. | | Uses | 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. | | Uses | 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. | | Uses | 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. | | Preparation | to 24 g (0.16 mol) of t-butyldimethylchlorosilane
at 23°C under argon is added 14 mL (0.16 mol) of
trifluoromethanesulfonic acid dropwise. The solution is heated
at 60°C for 10 h, at which time no further hydrogen chloride
evolves (removed through a bubbler). The resulting product is
distilled under reduced pressure: 34 g (80% yield) of TBDMS
triflate; bp 60°C/7 mmHg. |
| | Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester Preparation Products And Raw materials |
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