Triisopropylsilyl trifluoromethanesulfonate

Base Information

• Chemical Name: Triisopropylsilyl trifluoromethanesulfonate
• CAS No.: 80522-42-5
• Molecular Formula: C10H21F3O3SSi
• Molecular Weight: 306.422
• Hs Code.: 29319090
• European Community (EC) Number: 638-988-6
• DSSTox Substance ID: DTXSID10369150
• Nikkaji Number: J364.634C
• Wikidata: Q72513669
• Mol file: 80522-42-5.mol

Synonyms:Triisopropylsilyl trifluoromethanesulfonate;80522-42-5;Triisopropylsilyl triflate;Trifluoromethanesulfonic acid triisopropylsilyl ester;triisopropylsilyltrifluoromethanesulfonate;triisopropylsilyl-trifluoromethanesulfonate;triisopropylsilyl trifluoromethanesulphonate;tri(propan-2-yl)silyl trifluoromethanesulfonate;TIPS triflate;Methanesulfonic acid, trifluoro-, tris(1-methylethyl)silyl ester;Triisopropylsilyl trifluoromethanesulfonate, 97%;tris(propan-2-yl)silyl trifluoromethanesulfonate;tips-otf;TIPSOTf;i-Pr3SiOTf;MFCD00009913;(i-Pr)3SiOTf;triisopropylsilyltriflate;triisopropylsilanyl triflate;C10H21F3O3SSi;SCHEMBL114743;DTXSID10369150;CS-B0888;AKOS008901285;FS-4750;triisopropylsilyl trifluoromethylsulfonate;triisopropylsilyltrifluoromethanesulphonate;triisopropylsilyl-trifluoromethyl sulfonate;triisopropylsilyltrifluoromethane sulfonate;triisopropysilyl trifluoromethane-sulfonate;triisopropysilyl trifluoromethanesulphonate;Triisopropylsilyl trifluoromethane sulfonate;triisopropylsilyl trifluoromethane-sulfonate;triisopropylsilyl-trifluoro-methanesulfonate;triisopropylsilyl-trifluoromethane sulfonate;Triisopropylsilyltrifluoromethane sulphonate;tri-isopropylsilyl trifluoromethane sulfonate;FT-0641768;T1588;tri-iso-propylsilyl trifluoromethane sulfonate;EN300-6762257;A839932;tris(1-methylethyl)silyl trifluoromethanesulfonate

Chemical Property of Triisopropylsilyl trifluoromethanesulfonate

Chemical Property:

• Appearance/Colour: clear light brown to orange-brown liquid
• Vapor Pressure: 0.03mmHg at 25°C
• Refractive Index: n20/D 1.415(lit.)
• Boiling Point: 252.9 °C at 760 mmHg
• Flash Point: 106.8 °C
• PSA: 51.75000
• Density: 1.117 g/cm³
• LogP: 5.10890
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with chloroform and ethyl acetate.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 306.09327672
• Heavy Atom Count: 18
• Complexity: 347

Purity/Quality:

99.9% ^*data from raw suppliers

Triisopropylsilyl trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-28A-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F
• Physical properties: Colorless oil; bp 83–87 °C/1.7 mmHg; d 1.173 g cm?3.
• Uses: 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. 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.

Technology Process of Triisopropylsilyl trifluoromethanesulfonate

There total 4 articles about Triisopropylsilyl trifluoromethanesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

chlorotriisopropylsilane (6485-79-6) + trifluorormethanesulfonic acid (1493-13-6) → triisopropylsilyl trifluoromethanesulfonate (80522-42-5)

Guidance literature:

at 22 ℃; for 16h;

DOI:10.1016/S0040-4039(01)81930-4

Reference yield:

trifluorormethanesulfonic acid (1493-13-6) + allyl triisopropylsilane (24400-84-8) → triisopropylsilyl trifluoromethanesulfonate (80522-42-5)

Guidance literature:

In dichloromethane; at 0 ℃; for 2h;

DOI:10.1055/s-1997-1421

Reference yield:

triisopropylsilyl chloride (13154-24-0) + trifluorormethanesulfonic acid (1493-13-6) → triisopropylsilyl trifluoromethanesulfonate (80522-42-5)

Guidance literature:

at 60 ℃; for 10h;

DOI:10.1246/bcsj.63.1039 DOI:10.1016/S0040-4039(00)61843-9

upstream raw materials:

chlorotriisopropylsilane

trifluorormethanesulfonic acid

triisopropylsilyl chloride

allyl triisopropylsilane

Downstream raw materials:

(2,2-Dimethyl-1-methylene-propoxy)-triisopropyl-silane

3-Methyl-5-<(triisopropylsilyl)oxy>biphenyl-2-yl phenyl ketone

(E)-ethyl 4-((triisopropylsilyl)oxy)penta-2,4-dienoate

(1R,2R)-2-(triisopropylsilyloxy)cyclohexanol

Refernces

• 1、 Neumeyer, Markus,Brückner, Reinhard. "Establishing Consensus Stereostructures for the Naphthoquinonopyrano-γ-lactone Natural Products (–)-Arizonin B1 and (–)-Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa-Pictet–Spengler Cyclizations by Protective-Group Optimization". . p. 2512 - 2539. Retrieved 2017/05/15.
• 2、 Sancho, Amador Garcia,Wang, Xiao,Sui, Bin,Curran, Dennis P.. "Comparison of the relative reactivities of the triisopropylsilyl group with two fluorous analogs". experimental part. p. 1035 - 1040. Retrieved 2009/12/05.