tris(propan-2-yl)silyl trifluoromethanesulfonate

• ChemBase ID: 148359
• Molecular Formular: C10H21F3O3SSi
• Molecular Mass: 306.4176496
• Monoisotopic Mass: 306.09327672
• SMILES: CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F
• Canonical SMILES: CC([Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F)C
• InChI: InChI=1S/C10H21F3O3SSi/c1-7(2)18(8(3)4,9(5)6)16-17(14,15)10(11,12)13/h7-9H,1-6H3
• InChIKey: LHJCZOXMCGQVDQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(propan-2-yl)silyl trifluoromethanesulfonate
• IUPAC Traditional name: triisopropylsilyl trifluoromethanesulfonate
• Synonyms: TIPS triflate; Trifluoromethanesulfonic acid triisopropylsilyl ester; Triisopropylsilyl triflate; Triisopropylsilyl trifluoromethanesulfonate; Wacker Silane IP3-triflate; TIPS-OTf; Triisopropylsilyl trifluoromethanesulfonate; TIPS 三氟甲磺酸酯; 三异丙基甲硅烷基三氟甲磺酸酯; 三氟甲磺酸三异丙基硅基酯; 三异丙基硅基三氟甲磺酸酯; 三异丙基硅基三氟甲磺酸酯; 三异丙基甲硅烷基三氟甲烷磺酸盐

Database IDs

• CAS Number: 80522-42-5
• EC Number: 000-000-0
• MDL Number: MFCD00009913
• Beilstein Number: 3591541
• PubChem SID: 162242535; 24846002; 24854929
• PubChem CID: 2724529

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.1533
• LogD (pH = 7.4): 5.1533
• Log P: 5.1533
• Molar Refractivity: 60.4432 cm^3
• Polarizability: 26.423628 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Boiling Point: 45-46 °C/0.03 mmHg; 45-46°C/0.03mm
• Flash Point: 100°C(212°F); 103 °C; 217.4 °F
• Density: 1.136; 1.14 g/mL at 25 °C(lit.)
• Refractive Index: 1.4150; n20/D 1.415(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; 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 3265 8/PG 2

Product Information

• Purity: ≥98.0% (T); 95+%; 97%
• Grade: produced by Wacker; purum
• Linear Formula: CF3SO3Si[CH(CH3)2]3

DETAILS

Sigma Aldrich - 248460

Application
Used to prepare silyloxy acetylenes from lithium acetylides; the silyloxy acetylenes were then employed in protic acid-promoted cyclizations of arenes, alkynes and olefins.1
Packaging
10, 50 g in glass bottle

Sigma Aldrich - 91746

Other Notes
Reagent for the smooth introduction of the TIPS group1,2,3,4; Review5

REFERENCES

• Reagent for introduction of the triisopropylsilyl (TIPS) group: Tetrahedron Lett., 22, 3455 (1981); compare Chlorotriisopropylsilane, A17376, and Appendix 4. For general reactions of silyl triflates, see Trimethylsilyl trifluoromethanesulfonate, A12535.
• For use in the synthesis of 2-substituted benzothiopyran-4-ones, see: Synlett, 182 (1996):
  
• A method for protecting both H atoms of a primary amine consists of formation of the succinimide, followed by enolsilylation with TIPS-OTf, to form the 2,5-bis(triisopropylsiloxy)pyrroles. Deprotection can be effected by desilylation with dilute HCl, followed by hydrazinolysis: Tetrahedron Lett., 38, 2617 (1997).
• For a comprehensive review of the TIPS group in organic chemistry, see: Chem. Rev., 95, 1009 (1995).