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Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester

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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-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
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
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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.)
Flash point:
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
InChIKey
WLLIXJBWWFGEHT-UHFFFAOYSA-N
CAS DataBase Reference
69739-34-0(CAS DataBase Reference)
NIST Chemistry Reference
Tert-butyldimethylsilyl trifluoromethanesulfonate(69739-34-0)
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Safety Information

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
10-21
Hazard Note 
Flammable/Corrosive
TSCA 
No
HazardClass 
3
PackingGroup 
III
HS Code 
29310095

MSDS

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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

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.

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

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.

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

Preparation Products

Raw materials

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