2-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate

Base Information

• Chemical Name: 2-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate
• CAS No.: 164162-36-1
• Molecular Formula: C9H19F3O4SSi
• Molecular Weight: 308.394
• DSSTox Substance ID: DTXSID00576730
• Wikidata: Q72511207
• Mol file: 164162-36-1.mol

Synonyms:164162-36-1;2-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate;2-[tert-butyl(dimethyl)silyl]oxyethyl trifluoromethanesulfonate;2-(tert-Butyldimethylsilyl )oxyl alcohol trifluorin methanesulfonate;Methanesulfonic acid, 1,1,1-trifluoro-, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl ester;2-[(TERT-BUTYLDIMETHYLSILYL)OXY]ETHYL TRIFLUOROMETHANESULFONATE;2-(t-butyldimethylsilyl)oxyethyl triflate;SCHEMBL578097;DTXSID00576730;AKOS016009850;2-(-t-butyldimethylsilyl)oxyethyl triflate;2-(tert-butyldimethylsilyl)oxyethyl triflate;2-[(tert-Butyl)dimethylsiloxy]ethyl Triflate;A854483;2-(t-butyldimethylsilyloxy)ethyl trifluoromethanesulfonate;2-(tert-Butyldimethylsilyl)oxyl alcohol trifluorin methanesulfonate;2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl trifluoromethanesulfonate;Trifluoromethanesulfonicacid2-[[(Tert-Butyl)Dimethylsilyl]Oxy]Ethylester

Chemical Property of 2-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate

Chemical Property:

• Boiling Point: 253℃
• Flash Point: 107℃
• PSA: 60.98000
• Density: 1.172
• LogP: 3.95520
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 308.07254128
• Heavy Atom Count: 18
• Complexity: 365

Purity/Quality:

98% ^*data from raw suppliers

2-((TERT-BUTYLDIMETHYLSILYL)OXY)ETHYL TRIFLUOROMETHANESULFONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCCOS(=O)(=O)C(F)(F)F
• Uses: 2-(tert-butyldiMethylsilyl )oxyl alcohol trifluorin Methanesulfonate is used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Technology Process of 2-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate

There total 3 articles about 2-((tert-Butyldimethylsilyl)oxy)ethyl 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: 98.4%

trifluoromethylsulfonic anhydride (358-23-6) + 2-(tert-butyldimethylsilyloxy)ethanol (102229-10-7) → 2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate (164162-36-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -28 ℃; for 0.5h;

Reference yield:

trifluorormethanesulfonic acid (1493-13-6) + 2-(tert-butyldimethylsilyloxy)ethanol (102229-10-7) → 2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate (164162-36-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -18 - 20 ℃; for 1.33333h;

DOI:10.1002/(SICI)1099-1344(199901)42:1<29::AID-JLCR164>3.0.CO;2-5

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate (164162-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / 12 h / 0 - 30 °C

2: 2,6-dimethylpyridine / n-heptane / 2.75 h / -25 - -15 °C / Inert atmosphere

With 2,6-dimethylpyridine; triethylamine; In n-heptane;

upstream raw materials:

trifluorormethanesulfonic acid

2-(tert-butyldimethylsilyloxy)ethanol

trifluoromethylsulfonic anhydride

tert-butyldimethylsilyl chloride

Downstream raw materials:

40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin

Refernces

• 1、 -. "Purification method of everolimus". Paragraph 0069; 0070; 0071; 0072; 0073. . Retrieved 2019/01/24.
• 2、 -. "PROCESS FOR THE SYNTHESIS OF EVEROLIMUS AND INTERMEDIATES THEREOF". Page/Page column 23-24. . Retrieved 2016/04/09.