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HomeProduct name listTRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

Synonym(s):TIPS triflate;Trifluoromethanesulfonic acid triisopropylsilyl ester;Triisopropylsilyl triflate

  • CAS NO.:80522-42-5
  • Empirical Formula: C10H21F3O3SSi
  • Molecular Weight: 306.42
  • MDL number: MFCD00009913
  • EINECS: 638-988-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-08-30 19:07:15
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE Structural

What is TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE?

Chemical properties

clear light brown to orange-brown liquid

Physical properties

Colorless oil; bp 83–87 °C/1.7 mmHg; d 1.173 g cm?3.

The Uses of TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

Triisopropylsilyl Trifluoromethanesulfonate is a highly reactive silylating agent and Lewis acid capable of converting primary and secondary alcohols to the corresponding triisopropylsilyl ethers and converting ketones and lactones into their enol silyl ethers; protection of terminal alkynes; promoting conjugate addition of alkynylzinc compounds to α,β-enones; preparation of (triisopropylsilyl)diazomethane, participating in the following (but not limited to) reactions: Silylation of Alcohols, Formations of Enol Silyl Ethers, Alkynyltriisopropylsilanes, Conjugate Addition of Alkynylzinc Bromides, (Triisopropylsilyl)diazomethane, Triisopropylsiloxycarbonyl (Tsoc) and BIPSOP Protecting Groups for Amines, TIPS Protection for Oxazoles/Regioselective Trapping of C-2 Oxazole Anions, Benzannulation Using Triisopropylsilyl Vinyl Ketenes, Cyclization of 1-Silyloxy-1,5-diynes, Desymmetrization of Tartaric Acid Esters etc.

The Uses of TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

Triisopropylsilyl trifluoromethanesulfonate is used as a reagent for the introduction of triisopropylsilyl(TIPS) group in organic synthesis. It is involved in the synthesis of 2-substituted benzothiopyran-4-ones and silyloxy acetylenes. As a protecting group in organic synthesis, it is utilized especially for the protection of primary amines. Furthermore, it plays an important role in Takahashi Taxol total synthesis or for chemical glycosylation reactions.

Preparation

To 38.2 g (0.242 mol) of triisopropylsilane at 0°C under argon is added 23.8 mL (0.266 mol) of trifluoromethanesulfonic acid dropwise. The solution is stirred at 22°C for 16 h, at which time no further hydrogen gas evolves (removed through a bubbler). The resulting product is distilled through a 30-cm vacuum jacketed Vigreux column under reduced pressure: 71.7 g (97% yield) of TIPS triflate; bp 83–87°C/1.7 mmHg.

Properties of TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

Boiling point: 45-46 °C/0.03 mmHg
Density  1.14 g/mL at 25 °C (lit.)
refractive index  n20/D 1.415(lit.)
Flash point: 213 °F
storage temp.  under inert gas (nitrogen or Argon) at 2-8°C
solubility  Miscible with chloroform and ethyl acetate.
form  Liquid
color  Clear light brown to orange-brown
Specific Gravity 1.14
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents
Sensitive  Moisture Sensitive
BRN  3591541
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
CAS DataBase Reference 80522-42-5(CAS DataBase Reference)

Safety information for TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P363:Wash contaminated clothing before reuse.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

InChIKey LHJCZOXMCGQVDQ-UHFFFAOYSA-N
SMILES C(F)(F)(F)S(O[Si](C(C)C)(C(C)C)C(C)C)(=O)=O

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