4-(Trifluoromethyl)phenyl trifluoromethanesulfonate

Base Information

• Chemical Name: 4-(Trifluoromethyl)phenyl trifluoromethanesulfonate
• CAS No.: 146397-87-7
• Molecular Formula: C8H4 F6 O3 S
• Molecular Weight: 294.174
• Hs Code.: 2904990090
• DSSTox Substance ID: DTXSID30441866
• Nikkaji Number: J817.351F
• Wikidata: Q82258852
• Mol file: 146397-87-7.mol

Synonyms:146397-87-7;4-(trifluoromethyl)phenyl trifluoromethanesulfonate;4-(Trifluoromethyl)phenyl trifluoromethanesulphonate;[4-(trifluoromethyl)phenyl] trifluoromethanesulfonate;Methanesulfonic acid, 1,1,1-trifluoro-, 4-(trifluoromethyl)phenyl ester;SCHEMBL408478;DTXSID30441866;MFCD07784330;AKOS040767392;BS-52717;E83923;4-(Trifluoromethyl)phenol trifluoromethanesulfonate;A808502;[4-(trifluoromethyl)phenyl] tris(fluoranyl)methanesulfonate;trifluoromethanesulfonic acid [4-(trifluoromethyl)phenyl] ester

Chemical Property of 4-(Trifluoromethyl)phenyl trifluoromethanesulfonate

Chemical Property:

• Vapor Pressure: 0.042mmHg at 25°C
• Refractive Index: 1.426
• Boiling Point: 246.9°Cat760mmHg
• Flash Point: 103.1°C
• PSA: 51.75000
• Density: 1.595g/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: 371

Purity/Quality:

98% ^*data from raw suppliers

p-(Trifluoromethyl)phenylTriflate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi:

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(F)(F)F)OS(=O)(=O)C(F)(F)F
• Uses: p-(Trifluoromethyl)phenyl Triflate is used as a reactant in the design of PHOX ligands, used in the synthesis of pharmaceutical agents requiring single enantiomers. Particularly used in asymmetric Heck reaction.

Technology Process of 4-(Trifluoromethyl)phenyl trifluoromethanesulfonate

There total 5 articles about 4-(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: 98.0%

4-hydroxybenzotrifluoride (402-45-9) + trifluoromethylsulfonic anhydride (358-23-6) → p-(trifluoromethyl)phenyl trifluoromethanesulfonate (146397-87-7)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1021/jacs.6b12663

Reference yield: 88.0%

2,2-difluoro-2-(fluorosulfonyl)acetate (680-15-9) + 4-iodophenyl trifluoromethanesulfonate (109586-39-2) → p-(trifluoromethyl)phenyl trifluoromethanesulfonate (146397-87-7)

Guidance literature:

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

Reference yield: 85.0%

4-hydroxybenzotrifluoride (402-45-9) + trifluorormethanesulfonic acid (1493-13-6) → p-(trifluoromethyl)phenyl trifluoromethanesulfonate (146397-87-7)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c00313

upstream raw materials:

4-hydroxybenzotrifluoride

trifluoromethylsulfonic anhydride

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

4-iodophenyl trifluoromethanesulfonate

Downstream raw materials:

4,4'-bis(trifluoromethyl)biphenyl

phenyl[4-(trifluoromethyl)phenyl]methanone

phenyl(4-trifluoromethylphenyl)amine

1-(4-trifluoromethyl-phenyl)-cyclohexanecarbonitrile

Refernces

• 1、 Zhu, Zhaodong,Gong, Yuxin,Tong, Weiqi,Xue, Weichao,Gong, Hegui. "Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage". supporting information. p. 2158 - 2163. Retrieved 2021/04/05.
• 2、 Cornella, Josep,Peciukenas, Vytautas,Planas, Oriol. "Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts". supporting information. p. 11382 - 11387. Retrieved 2020/07/14.