2-(Trifluoromethyl)phenyl trifluoromethanesulfonate

Base Information

• Chemical Name: 2-(Trifluoromethyl)phenyl trifluoromethanesulfonate
• CAS No.: 199188-29-9
• Molecular Formula: C8H4F6O3S
• Molecular Weight: 294.174
• Hs Code.: 2905190098
• DSSTox Substance ID: DTXSID30445506
• Nikkaji Number: J893.052J
• Mol file: 199188-29-9.mol

Synonyms:199188-29-9;2-(TRIFLUOROMETHYL)PHENYL TRIFLUOROMETHANESULFONATE;[2-(trifluoromethyl)phenyl] trifluoromethanesulfonate;2-(Trifluoromethyl)phenyl trifluoromethanesulphonate;Methanesulfonic acid, 1,1,1-trifluoro-, 2-(trifluoromethyl)phenyl ester;SCHEMBL6207099;DTXSID30445506;Trifluoromethanesulfonic acid 2-(trifluoromethyl)phenyl ester

Chemical Property of 2-(Trifluoromethyl)phenyl trifluoromethanesulfonate

Chemical Property:

• Vapor Pressure: 0.032mmHg at 25°C
• Boiling Point: 251.626°C at 760 mmHg
• Flash Point: 105.98°C
• PSA: 51.75000
• Density: 1.596g/cm³
• LogP: 4.01460
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 293.97853413
• Heavy Atom Count: 18
• Complexity: 379

Purity/Quality:

97% ^*data from raw suppliers

2-(Trifluoromethyl)phenyltrifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(F)(F)F)OS(=O)(=O)C(F)(F)F
• Uses: 2-(Trifluoromethyl)phenyl trifluoromethanesulfonate is used in the green synthetic preparation of N-aryl sulfonamides under mild reaction conditions with palladium nanoparticles as reusable catalysts.

Technology Process of 2-(Trifluoromethyl)phenyl trifluoromethanesulfonate

There total 3 articles about 2-(Trifluoromethyl)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: 91.0%

trifluoromethylsulfonic anhydride (358-23-6) + 2-(trifluoromethyl)phenol (444-30-4) → 2-trifluoromethyl-1-trifluoromethanesulfonyloxybenzene (199188-29-9)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 48h;

DOI:10.1039/b406803c

Reference yield: 84.0%

2,2-difluoro-2-(fluorosulfonyl)acetate (680-15-9) + 2-iodophenyltrifluoromethanesulfonic acid (129112-26-1) → 2-trifluoromethyl-1-trifluoromethanesulfonyloxybenzene (199188-29-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; In N,N-dimethyl-formamide; at 70 ℃; for 4h;

Reference yield:

2-Iodophenol (533-58-4) → 2-trifluoromethyl-1-trifluoromethanesulfonyloxybenzene (199188-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1.5 h, 2.) -78 deg C to r.t., overnight

2: 84 percent / CuI, HMPA / dimethylformamide / 4 h / 70 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

2,2-difluoro-2-(fluorosulfonyl)acetate

2-iodophenyltrifluoromethanesulfonic acid

trifluoromethylsulfonic anhydride

2-(trifluoromethyl)phenol

Downstream raw materials:

diisopropyl 1-[2-(trifluromethyl)phenyl]-hydrazine-1,2-dicarboxylate

1-phenyl-1-(2-trifluoromethylphenyl)ethylene

2-trifluoromethyl-6-trifluoromethanesulphonylphenol

Refernces

• 1、 Dyke, Alan M.,Gill, Duncan M.,Harvey, Jeremy N.,Hester, Alison J.,Lloyd-Jones, Guy C.,Munoz, M. Paz,Shepperson, Ian R.. "Decoupling deprotonation from metalation: Thia-fries rearrangement". supporting information; experimental part. p. 5067 - 5070. Retrieved 2009/03/11.
• 2、 Qing, Feng-Ling,Fan, Junfa,Sun, Hong-Bin,Yue, Xiang-Jun. "First synthesis of ortho-trifluoromethylated aryl triflates". . p. 3053 - 3057. Retrieved 2007/10/03.