567-59-9

Upstream product

• 108-70-3 1,3,5-trichlorobenzene 
• 75-69-4 trichlorofluoromethane 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 2926-29-6 Langlois reagent 

Downstream Products

• 14379-95-4 α,α,α,2,4,6-hexachlorotoluene 
• 50-43-1 2,4,6-trichlorobenzoic acid 
• 23400-04-6 2,4,6-trichloro-benzoic acid amide 
• 86569-78-0 methyl 2,4,6-trichlorobenzoate 

Relevant academic research and scientific papers

Electrophotocatalytic Undirected C?H Trifluoromethylations of (Het)Arenes

Electrophotochemistry has enabled arene C?H trifluoromethylation with the Langlois reagent CF3SO2Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for the generation of the CF3 radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C?H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron-rich and electron-deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C?H trifluoromethylation was further achieved in flow with a modular electro-flow-cell equipped with an in-operando monitoring unit for on-line flow-NMR spectroscopy, providing support for the single electron transfer processes.

Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent

A large number of reagents have been developed for the synthesis of trifluoromethylated compounds. However, an ongoing challenge in trifluoromethylation reaction is the use of less expensive and practical trifluoromethyl sources. We report herein the unprecedented direct trifluoromethylation of (hetero)arenes using trifluoromethanesulfonic anhydride as a radical trifluoromethylation reagent by merging photoredox catalysis and pyridine activation. Furthermore, introduction of both the CF3 and OTf groups of the trifluoromethanesulfonic anhydride into internal alkynes to access tetrasubstituted trifluoromethylated alkenes was achieved. Since trifluoromethanesulfonic anhydride is a low-cost and abundant chemical, this method provides a cost-efficient and practical route to trifluoromethylated compounds.

A New Trifluoromethylating Agent: Synthesis of Polychlorinated (Trifluoromethyl)benzenes and 1,3-Bis(trifluoromethyl)benzenes and Conversion into Their Trichloromethyl Counterparts and Molecular Structure of Highly Strained Polychloro-m-xylenes

Mixtures of CCl3F and AlCl3 replace CF3 for H in polychlorobenzenes.Thus, by treatment of a solution of the suitable polychlorobenzene in CCl3F with AlCl3, the following compounds can be prepared: pentachloro- (2), 2,3,4,5-tetrachloro- (5), 2,3,4,6-tetrachloro- (8), 2,3,5,6-tetrachloro- (11), 2,3,4-trichloro- (14), 2,4,5-trichloro- (17), and 2,4,6-trichloro-1-(trifluoromethyl)benzene (20), as well as 4,5,6-trichloro- (31) and 2,4,6-trichloro-1,3-bis(trifluoromethyl)benzene (32).The reaction of the above-mentioned trifluoromethylated compounds with AlCl3 in CS2 yieldstheir trichloromethyl counterparts: 3, 6, 9, 12, 15, 18, 21, 34, and 36.The chlorination of 32 or 36 by means of Silberrad's reagent (SO2Cl2, AlCl3, and S2Cl2) affords perchloro-m-xylene (38), a new highly strained chlorocarbon whose synthesis was attempted repeatedly in the past. 9, 15, 17, and 21, when treated with oleum and then with water, are converted into 2,3,4,6-tetrachloro- (22), 2,3,4-trichloro- (23), 2,4,5-trichloro- (24), and 2,4,6-trichlorobenzoic acid (25), respectively; under similar treatment, 34, 36, and 38 give 4,5,6-trichloro- (33), 2,4,5-trichloro- (35), and tetrachloroisophthalic acid (39), respectively.The formation of the (trifluoromethyl)benzenes is discussed, and in this connection it has been found that CCl3F solutions of 3 and 18 in the presence of AlCl3 give back 2 and 17, respectively.Molecular structures of highly strained m-xylenes 36 and 38, as well as that of the much less strained 34, ascertained by X-ray analysis, are reported and commented.IR, UV, and NMR spectral data of the compounds synthesized are presented.The interesting UV spectrum of 21 is discussed.

NEW SYNTHESIS OF POLYCHLORO(TRIFLUOROMETHYL)BENZENES AND HIGHLY STRAINED POLYCHLORO(TRICHLOROMETHYL)BENZENES

Several polychloro(trifluoromethyl)benzenes have been prepared by treatment of the corresponding polychlorobenzenes with CCl3F and AlCl3.The resulting trifluoromethyl derivatives, by reaction with the same inorganic halide in CS2, give their trichloromethyl analogues.