tert-butyldimethylsilyl trifluoromethanesulfonate

• ChemBase ID: 94317
• Molecular Formular: C7H15F3O3SSi
• Molecular Mass: 264.3379096
• Monoisotopic Mass: 264.04632653
• SMILES: [Si](C(C)(C)C)(C)(C)OS(=O)(=O)C(F)(F)F
• Canonical SMILES: C[Si](C(C)(C)C)(OS(=O)(=O)C(F)(F)F)C
• InChI: InChI=1S/C7H15F3O3SSi/c1-6(2,3)15(4,5)13-14(11,12)7(8,9)10/h1-5H3
• InChIKey: WLLIXJBWWFGEHT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyldimethylsilyl trifluoromethanesulfonate
• IUPAC Traditional name: tert-butyldimethylsilyl trifluoromethanesulfonate
• Synonyms: (1,1-Dimethylethyl)dimethylsilyl Trifluoromethanesulfonate; Trifluoromethanesulfonic Acid (1,1-Dimethylethyl)dimethylsilyl ester; Trifluoromethanesulfonic Acid tert-Butyldimethylsilyl Ester; tert-Butyldimethylsilyl Triflate; tert-Butyldimethylsilyl Trifluoromethanesulfonate; Trifluoromethanesulfonic acid tert-butyldimethylsilylester; tert-Butyldimethylsilyl trifluoromethanesulfonate; Silane TBM2 triflate; TBDMS triflate; tert-Butyldimethylsilyl trifluoromethanesulphonate 97+%; Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester; TBDMS-OTf; TBDMS 三氟甲磺酸酯; 三氟甲磺酸叔丁基二甲基硅基酯; 叔丁基二甲基硅基三氟甲磺酸酯; 叔丁基二甲硅基三氟甲磺酸酯; 三氟甲烷磺酸叔丁基二甲基硅烷基酯

Database IDs

• CAS Number: 69739-34-0
• EC Number: 274-102-0
• MDL Number: MFCD00000405
• Beilstein Number: 2370068
• PubChem SID: 24853546; 24889549; 24850210; 162080971
• PubChem CID: 123564

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.8259
• LogD (pH = 7.4): 3.8259
• Log P: 3.8259
• Molar Refractivity: 46.83 cm^3
• Polarizability: 21.047956 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 65-67 °C/12 mmHg(lit.); 65-67°C/12mm; 65-67°C/12mm
• Flash Point: 36°C; 36°C(96°F); 37 °C; 98.6 °F
• Density: 1.151; 1.151 g/mL at 20 °C; 1.151 g/mL at 25 °C(lit.)
• Refractive Index: 1.385; 1.3860; n20/D 1.385(lit.)

Safety Information

• Storage Warning: Flammable/Corrosive/Store under inert gas/Keep Cold/Moisture Sensitive; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2920; UN2920
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 10-34; 10-34-37
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314-H335; H314-H318-H226
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); 97%; 98%
• Grade: produced by Wacker; purum; reagent grade
• Linear Formula: CF3SO3Si(CH3)2C(CH3)3

DETAILS

Apollo Scientific Ltd - PC1605

Electrophilic reagent for introduction of t-butyldimethylsilyl group. For a review see: Emde et al., Synthesis, 1982 , 1.

Sigma Aldrich - 226149

Application
This reagent was used to introduce a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane facilitating a room temperature Cope rearrangement to a 2-CF3-4,5-dihydrooxepin.1
Together with a thiolane promotes a rapid and efficient chalcogenide-Morita-Baylis-Hillman reaction.
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 16747

Other Notes
prices for bulk quantities on request

Sigma Aldrich - 91742

Other Notes
Powerful and strongly electrophilic reagent for the introduction of the tert-butyl-dimethylsilyl group1,2,3,4; Reviews5

Toronto Research Chemicals - B691775

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 us

REFERENCES

• Hua, D.H. et al.L e-ROS Encyc. Reag. Org. Synth., No pp. given (2001)
• Suzuki, T. et al.: Synthesis, 4, 555 (2001)
• Powerful silylating agent (see Appendix 4) and Lewis acid; compare tert-Butyldimethylchlorosilane, A13064 and 3429. Silylation of hindered alcohols can be effected with TBDMS-OTf and 2,6-lutidine, where other reagents are unsuccessful: Tetrahedron Lett., 22, 3455 (1981).
• Has been used in a sequence for the conversion of N-Boc to N-Cbz: Tetrahedron Lett., 26, 5543 (1985). For an alternative method for this transformation, see Benzyl 2,2,2-trichloroacetimidate, A12387.
• Treatment of ɑ?-unsaturated esters containing a suitably-placed ketone function with the reagent and triethylamine results in tandem intramolecular Michael-aldol reactions to give cyclobutanone derivatives: J. Am. Chem. Soc., 115, 8107 (1993).
• For general reactions of trialkylsilyl perfluoroalkanesulfonates, see Trimethylsilyl trifluoromethanesulfonate, A12535; reviews: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).