4,5-Dimethoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate

Base Information

• Chemical Name: 4,5-Dimethoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate
• CAS No.: 866252-52-0
• Molecular Formula: C₁₂H₁₇F₃O₅SSi
• Molecular Weight: 358.411
• Hs Code.: 29319090
• European Community (EC) Number: 679-878-8
• DSSTox Substance ID: DTXSID90583079
• Nikkaji Number: J2.231.763F
• Wikidata: Q82474596
• Mol file: 866252-52-0.mol

Synonyms:4,5-Dimethoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate;866252-52-0;(4,5-dimethoxy-2-trimethylsilylphenyl) trifluoromethanesulfonate;4,5-Dimethoxy-2-(trimethylsilyl)phenyl Triflate;MFCD15072159;DTXSID90583079;DLUVZOFWZNLGTJ-UHFFFAOYSA-N;AKOS015852939;BS-44042;SY054551;D3883;T71416;4,5-Dimethoxy-2-(trimethylsilyl)phenylTrifluoromethanesulfonate;Trifluoromethanesulfonic Acid 4,5-Dimethoxy-2-(trimethylsilyl)phenyl Ester

Chemical Property of 4,5-Dimethoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4740-1.4780
• PSA: 70.21000
• LogP: 3.55820
• Storage Temp.: <0°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 358.05180583
• Heavy Atom Count: 22
• Complexity: 469

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,5-Dimethoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate >90.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1OC)[Si](C)(C)C)OS(=O)(=O)C(F)(F)F

Technology Process of 4,5-Dimethoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate

There total 5 articles about 4,5-Dimethoxy-2-(trimethylsilyl)phenyl 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: 63.0%

Hexamethyldisiloxane (107-46-0) + trifluoromethylsulfonic anhydride (358-23-6) + 2-bromo-4,5-dimethoxyphenol (129103-69-1) → 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (866252-52-0)

Guidance literature:

Hexamethyldisiloxane; 2-bromo-4,5-dimethoxyphenol; In tetrahydrofuran; at 70 ℃; for 5h;

With n-butyllithium; In tetrahydrofuran; cyclohexane; at -100 - -82 ℃; for 0.5h;

trifluoromethylsulfonic anhydride; In tetrahydrofuran; cyclohexane; at -100 - -80 ℃;

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + 4,5-dimethoxy-2-trimethylsilylphenol (1276113-16-6) → 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (866252-52-0)

Guidance literature:

4,5-dimethoxy-2-trimethylsilylphenol; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

trifluoromethylsulfonic anhydride; In tetrahydrofuran; at -78 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2019.04.033

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (866252-52-0)

Guidance literature:

1,1,1,3,3,3-hexamethyl-disilazane; 4,5-dimethoxy-2-halophenol; In tetrahydrofuran; for 3h; Inert atmosphere; Reflux;

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

trifluoromethylsulfonic anhydride; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.8b02560

upstream raw materials:

Hexamethyldisiloxane

trifluoromethylsulfonic anhydride

2-bromo-4,5-dimethoxyphenol

1,1,1,3,3,3-hexamethyl-disilazane

Downstream raw materials:

(5,6-dimethoxybenzofuran-2-yl)(phenyl)methanone

C₂₀H₂₃NO₄

Refernces

• 1、 Lei, Meng,Miao, Hang,Wang, Xueyuan,Zhang, Wen,Zhu, Chengjian,Lu, Xiaqiang,Shen, Jian,Qin, Yanru,Zhang, Haoyang,Sha, Sijia,Zhu, Yongqiang. "Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent". supporting information. p. 1389 - 1392. Retrieved 2019/04/30.