5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate

Base Information

• Chemical Name: 5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate
• CAS No.: 129946-88-9
• Molecular Formula: C13H8F3S^.CF3O3S
• Molecular Weight: 402.338
• Hs Code.: 29349990
• European Community (EC) Number: 627-294-9
• DSSTox Substance ID: DTXSID10380542
• Mol file: 129946-88-9.mol

Synonyms:129946-88-9;S-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate;5-(Trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate;5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate;MFCD00236132;S-(Trifluoromethyl)dibenzothiophenium triflate;trifluoromethanesulfonate;5-(trifluoromethyl)dibenzothiophen-5-ium;5-(Trifluoromethyl)dibenzothiophenium 1,1,1-Trifluoromethanesulfonate;SCHEMBL115549;C14H8F6O3S2;DTXSID10380542;AKOS016003855;CS-W007716;DS-14835;SY029819;AM20020378;FT-0643119;J-005727;S-(trifluoromethyl)dibenzothiophenium trifluoromethane sulfonate;S-(Trifluoromethyl)dibenzothiophenium trifluoromethane-sulfonate;S-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulphonate;5-(trifluoromethyl)dibenzo[b,d]thiophenium trifluoromethanesulfonate;5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate, 97%;S-(TRIFLUOROMETHYL)DIBENZOTHIOPHENIUMTRIFLUOROMETHANESULFONATE;Trifluoromethanesulfonate 5-(trifluoromethyl)dibenzothiophen-5-ium;trifluoromethanesulfonate 5-(trifluoromethyl)dibenzothiophen-5-ium;5-(trifluoromethyl)-5H-dibenzo[b,d]thiophenium trifluoromethanesulfonate;5-(Trifluoromethyl)dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate;Dibenzothiophenium, 5-(trifluoromethyl)-, 1,1,1-trifluoromethanesulfonate (1:1)

Chemical Property of 5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate

Chemical Property:

• Appearance/Colour: White to pale brown crystalline powder
• Melting Point: 155 °C
• PSA: 90.88000
• Density: 7 g/cm³
• LogP: 5.35530
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 0
• Exact Mass: 401.98190543
• Heavy Atom Count: 25
• Complexity: 412

Purity/Quality:

99% ^*data from raw suppliers

5-(Trifluoromethyl)dibenzothiophenium1,1,1-Trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3[S+]2C(F)(F)F.C(F)(F)(F)S(=O)(=O)[O-]
• Uses: S-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate. Electrophilic trifluoromethylation in ionic liquids. Used in the stereoselective preparation of trifluoromethylalkynes by trifluoromethylation of terminal alkynes using Umemoto′s reagent and a copper catalyst. 5-(Trifluoromethyl)dibenzothiophenium 1,1,1-Trifluoromethanesulfonate is used in the synthesis of substituted isoxazolines. Also used in the synthesis of β-ketophosphonate derivatives as building blocks in automated syntheses.

Technology Process of 5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate

There total 17 articles about 5-(Trifluoromethyl)dibenzothiophenium 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: 92.0%

sodium triflate (2926-30-9) + S-(Trifluoromethyl)dibenzothiophenium hydrogen sulfate → Umemoto's reagent (129946-88-9)

Guidance literature:

In acetonitrile; at 60 ℃; for 1.5h;

DOI:10.1016/S0022-1139(98)00276-0

Reference yield: 83.0%

trifluorormethanesulfonic acid (1493-13-6) + 2-<(trifluoromethyl)thio>biphenyl (129922-51-6) → Umemoto's reagent (129946-88-9)

Guidance literature:

With fluorine; In trichlorofluoromethane; at 0 ℃;

DOI:10.1021/ja00059a009

Reference yield: 75.0%

trifluoromethylsulfonic anhydride (358-23-6) + 2-<(trifluoromethyl)sulfinyl>biphenyl (129922-49-2) → Umemoto's reagent (129946-88-9)

Guidance literature:

In 1,1,2-Trichloro-1,2,2-trifluoroethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(00)94447-2

upstream raw materials:

trifluorormethanesulfonic acid

2-<(trifluoromethyl)thio>biphenyl

C₁₃H₉F₅S

trifluoromethylsulfonic anhydride

Downstream raw materials:

2-(trifluoromethyl)cyclohexanone

3,3,3-trifluoro-1-phenylpropyne

2-Methyl-2-(trifluoromethyl)cyclohexanone

ethyl 3,3,3-trifluoro-2-phenylpropionate

Refernces

• 1、 Mace, Yohan,Raymondeau, Benoit,Pradet, Charlotte,Blazejewski, Jean-Claude,Magnier, Emmanuel. "Benchmark and Solvent-Free preparation of sulfonium salt based electrophilic trifluoromethylating reagents". experimental part. p. 1390 - 1397. Retrieved 2009/08/07.
• 2、 Umemoto, Teruo,Ishihara, Sumi. "Effective methods for preparing S-(trifluoromethyl)dibenzothiophenium salts". . p. 181 - 187. Retrieved 2007/10/03.