| Identification | More | [Name]
Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester | [CAS]
69739-34-0 | [Synonyms]
SILANE TBM2 TRIFLATE
TBDMS TRIFLATE
TBMDS-OTF
TBS-OTF
T-BUTYLDIMETHYLSILYL TRIFLUOROMETHANESULFONATE
T-BUTYLDIMETHYLSILYLTRIFLUOROMETHANE-SULPHONATE
TERT-BUTYLDIMETHYLSILYL TRIFLATE
TERT-BUTYLDIMETHYLSILYL TRIFLUOROMETHANESULFONATE
TERT-BUTYLDIMETHYLSILYL TRIFLUOROMETHANESULPHONATE
TRIFLUOROMETHANESULFONIC ACID TERT-BUTYLDIMETHYLSILYL ESTER
Methanesulfonic acid, trifluoro-, (1,1-dimethylethyl)dimethylsilyl ester
t-Butyldimethylsilyl triflate
t-butyldimethylsilyltrifluormethansulfonate
t-Butylmethylsilyl triflate
tert-Buthyldimethylsilyl trifluoromethane sulfonate
TRIFLUOROMETHANESULFONIC ACID*T-BUTYLDIM ETHYLSILYL
tert-BUTYLDIMETHYLSILYL TRIFLUOROMETHANESULFONATE 98%
t-Butyldimethylsilyltrifluoromethanesulfonate,98%
tbdms-otf
tert-Butyldimethylsilyl trifluoromethane | [EINECS(EC#)]
274-102-0 | [Molecular Formula]
C7H15F3O3SSi | [MDL Number]
MFCD00000405 | [Molecular Weight]
264.34 | [MOL File]
69739-34-0.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to yellow fuming liquid | [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 | [color ]
Clear colorless to yellow | [Specific Gravity]
1.151 | [Water Solubility ]
DECOMPOSES | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [Sensitive ]
Moisture Sensitive | [BRN ]
2370068 | [InChIKey]
WLLIXJBWWFGEHT-UHFFFAOYSA-N | [CAS DataBase Reference]
69739-34-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Tert-butyldimethylsilyl trifluoromethanesulfonate(69739-34-0) |
| Safety Data | Back Directory | [Hazard Codes ]
C,F | [Risk Statements ]
R10:Flammable.
R34:Causes burns.
R37:Irritating to the respiratory system. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S25:Avoid contact with eyes .
S16:Keep away from sources of ignition-No smoking . | [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 |
| Hazard Information | Back Directory | [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]
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. |
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