392-83-6

Usage

Chemical Properties

clear colorless to brown liquid

InChI:InChI=1/C7H4BrF3/c8-6-4-2-1-3-5(6)7(9,10)11/h1-4H

Upstream product

• 98-08-8 α,α,α-trifluorotoluene 
• 393-36-2 4-bromo-3-(trifluoromethyl)aniline 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 56-23-5 tetrachloromethane 
• 108-86-1 bromobenzene 
• 2314-97-8 iodotrifluoromethane 
• 2966-50-9 silver trifluoroacetate 
• 75-61-6 dibromodifluoromethane 
• 444-29-1 2-iodo(trifluoromethyl)benzene 
• 88-65-3 2-bromobenzoic-acid 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 433-97-6 2-trifluoromethylbenzoic acid 
• 1319750-54-3 C₁₂H₁₈BrN₃ 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Downstream Products

• 433-97-6 2-trifluoromethylbenzoic acid 
• 124401-04-3 3-(2-(Trifluoromethyl)phenyl)-1,2-benzisothiazole 1,1-Dioxide 
• 123846-76-4 N-Pyridin-3-yl-N-(2-trifluoromethyl-phenyl)-acetamide 
• 312-92-5 trimethyl(2-(trifluoromethyl)phenyl)silane 
• 85491-17-4 (chloromethyl)(2-(trifluoromethyl)phenyl)dimethylsilyl 
• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 
• 88444-77-3 1-(2,2-dichloro-1-fluoroethenyl)-2-(trifluoromethyl)benzene 
• 82299-61-4 C₁₅H₂₄F₃N₂P 
• 142335-87-3 2-(1,1-dimethylethoxy)-5-<(2-trifluoromethyl)phenyl>furan 
• 13333-97-6 o-trifluoromethylbenzenethiol 
• 25688-42-0 tris(2-(trifluoromethyl)phenyl)phosphane 
• 82299-62-5 C₇H₄Cl₂F₃P 
• 13630-19-8 2-methylbenzotrifluoride 
• 79756-81-3 (+/-)-α-(o-(trifluoromethyl)phenyl)ethyl alcohol 

Relevant academic research and scientific papers

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Direct bromodeboronation of arylboronic acids with CuBr2 in water

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.

Synthesis method of 2-bromo-5-fluorobenzotrifluoride

The invention relates to a synthesis method of 2-bromo-5-fluorobenzotrifluoride. The synthesis method comprises the following steps: with benzotrifluoride as a raw material, mixing benzotrifluoride with sulfuric acid, potassium bromide, cuprous bromide and a catalyst, and carrying out a bromination reaction to obtain 2-bromobenzotrifluoride; putting the obtained 2-bromobenzotrifluoride into a DMSOsolvent, adding potassium fluoride and KCoF4, and carrying out a fluorination reaction so as to obtain 2-bromo-5-fluorobenzotrifluoride. According to the method, trifluorotoluene is used as the raw material; the method is a brand-new synthetic route; bromination and fluorination conditions are mild; reaction yield is high; used raw materials are easy to purchase and low in price; and thus, the method has relatively high industrial application value.

Visible-light-induced Pd-catalyzed: Ortho -trifluoromethylation of acetanilides with CF3SO2Na under ambient conditions in the absence of an external photocatalyst

A visible-light-induced Pd-catalyzed ortho-trifluoromethylation of acetanilides with CF3SO2Na was developed. The reaction proceeded smoothly at room temperature in air without any external photocatalyst or additive, providing the desired products in moderate to good yields with good functional group tolerance and regioselectivity.

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

Visible-Light photoredox decarboxylation of perfluoroarene iodine(III) Trifluoroacetates for C-H trifluoromethylation of (Hetero)arenes

A scalable and operationally simple decarboxylative trifluoromethylation of (hetero)arenes with easily accessible C6F5I(OCOCF3)2 under photoredox catalysis has been developed. This method is tolerant of various (hetero)arenes and functional groups. Notably, C6F5I is recycled from the decarboxylation reaction and further used for the preparation of C6F5I(OCOCF3)2. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the application of trifluoroacetic acid in trifluoromethylation reactions.

Synthesis method of 2-bromo-5-fluorobenzotrifluoride

The invention relates to a synthesis method of 2-bromo-5-fluorobenzotrifluoride, belonging to the field of chemical synthesis. The method uses orthotrifluoromethyl aniline as the initial raw material, and comprises the following steps: (1) Sandmeyer bromination reaction; (2) nitration reaction; (3) catalytic hydrogenation reduction reaction; and (4) diazotization fluorination reaction. According to the method, the orthotrifluoromethyl aniline used as the raw material is subjected to Sandmeyer reaction bromination, nitration, hydrogenation reduction and diazotization fluorination to finally synthesize the 2-bromo-5-fluorobenzotrifluoride. The 2-bromo-5-fluorobenzotrifluoride product has the advantages of high purity (up to 99.0% or above), fewer impurity varieties and stable quality and properties.

Method for synthesizing 2-Bromobenzotrifluoride

The present invention provides a method for synthesizing 2-Bromobenzotrifluoride, and the method comprises the following steps: A) 2-Aminotrifluoromethylbenzene, hydrobromic acid and sodium nitrite are mixed for reaction to obtain a diazonium salt solution; and B) the diazonium salt solution, cuprous bromide and hydrobromic acid are mixed for reaction to obtain the 2-Bromobenzotrifluoride. The method overcomes the defects of high cost, many product impurities and the like in prior art, cheap and accessible raw materials are used, solvent recovery effect is good, yield is high, product content is high, the 2-Bromobenzotrifluoride can be synthesized in one step, compared with other routes, meta and para isomers are less, and the production cost is low.

Introducing a new radical trifluoromethylation reagent

Perfluoro-3-ethyl-2,4-dimethyl-3-pentyl radical (PPFR) is a persistent radical stable at room temperature, but easily decomposes at 90 °C to produce a CF3 radical which is able to react with a variety of aromatic compounds to afford the corresponding trifluoromethyl derivatives, usually as mixtures of regioisomers in good to excellent overall yields.

Direct synthesis of a trifluoromethyl copper reagent from trifluoromethyl ketones: Application to trifluoromethylation

Being economic with fluorine: The direct synthesis of CuCF3 from a cuprate reagent and trifluoromethyl ketones, as one of the most economical and efficient trifluoromethyl sources, was accomplished. The advantages of this method are all of reagents employed are low-cost, operation is simple, and the yield of CuCF3 is virtually quantitative (see scheme). Furthermore, three types of trifluoromethylations smoothly proceeded to provide the corresponding products in high yields. Copyright