401-78-5

Usage

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

Uses

1-Bromo-3-(trifluoromethyl)benzene is used in the synthesis of calcium channel inhibitors for inflammatory and neuropathic pain.

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

Upstream product

• 98-08-8 α,α,α-trifluorotoluene 
• 98-16-8 3-trifluoromethylaniline 
• 108-86-1 bromobenzene 
• 2314-97-8 iodotrifluoromethane 
• 2966-50-9 silver trifluoroacetate 
• 364-12-5 4-bromo-1-iodo-2-(trifluoromethyl)benzene 
• 65-85-0 benzoic acid 
• 160911-82-0 1-Bromo-3-(ethylsulfanyl-difluoro-methyl)-benzene 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 7726-95-6 bromine 
• 585-76-2 m-bromobenzoic acid 
• 66920-03-4 S-ethyl 3-bromothiobenzoate 
• 160911-77-3 3-Bromo-dithiobenzoic acid ethyl ester 
• 7439-89-6 iron 

Downstream Products

• 396-84-9 2-(3-(trifluoromethyl)phenyl)quinoline 
• 4405-40-7 trimethyl(3-(trifluoromethyl)phenyl)silane 
• 394-80-9 [1]naphthyl-(3-trifluoromethyl-phenyl)-ether 
• 426-76-6 triphenyl-(3-trifluoromethyl-phenyl)-silane 
• 403-88-3 (3-ethyl-phenyl)-(3-trifluoromethyl-phenyl)-ether 
• 98-08-8 α,α,α-trifluorotoluene 
• 454-90-0 3-(trifluoromethyl)anisole 
• 328-98-3 3-(trifluoromethyl)phenyl methyl sulfide 
• 344-38-7 4-bromo-1-nitro-2-(trifluoromethyl)benzene 
• 595-88-0 tetrakis-(3-trifluoromethyl-phenyl)-silane 
• 1262-75-5 tetrakis(m-trifluoromethylphenyl)tin 
• 330-60-9 (4-chloro-phenyl)-(3-trifluoromethyl-phenyl)-ether 
• 426-74-4 phenyl-tris-(3-trifluoromethyl-phenyl)-silane 
• 330-58-5 phenyl m-α,α,α-trifluorotolyl ether 

Relevant academic research and scientific papers

Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines

The base-catalyzed isomerization of simple aryl halides is presented and utilized to achieve the 4-selective etherification, hydroxylation and amination of 3-bromopyridines. Mechanistic studies support isomerization of 3-bromopyridines to 4-bromopyridines proceedsviapyridyne intermediates and that 4-substitution selectivity is driven by a facile aromatic substitution reaction. Useful features of a tandem aryl halide isomerization/selective interception approach to aromatic functionalization are demonstrated. Example benefits include the use of readily available and stable 3-bromopyridines in place of less available and stable 4-halogenated congeners and the ability to converge mixtures of 3- and 5-bromopyridines to a single 4-substituted product.

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.

Efficient and practical 3-bromobenzotrifluoride synthesis method

The invention discloses an efficient and practical 3-bromobenzotrifluoride synthesis method, which comprises the following concrete steps that (1) acetic acid and water are added into a reaction container; then, 98-percent sulphuric acid is dropwise added; (2) benzotrifluoride is added; sodium bromide is added in batches; the temperature during the charging is controlled not to exceed 45 DEG C; (3) after the reaction is completed, the material temperature in the container is lowered to 30 DEG C or below; after the still standing, an organic layer A is separated out; meanwhile, a water layer Bis left; (4) an organic solvent is added into the water layer B; extraction is performed once; an organic layer C is separated out; (5) the organic layers A and C are merged; water is added into a mixed solution; after the stirring, still standing is performed in a liquid separating funnel; an upper layer water phase and a lower organic layer are separated; (6) the organic layer obtained in the step (5) is washed by a NaOH water solution; (7) the organic layer in the step (6) is subjected to operations such as separation and drying, 3-bromobenzotrifluoride can be obtained. The NaBrO3-H2SO4-CH3COOH system is adopted for reaction; three wastes (waste water, waste solid and waste gas) are few; high efficiency and practicability are realized.

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.

Copper-Promoted Conversion of Aromatic Amines into Trifluoromethylated Arenes: One-Pot Sandmeyer Trifluoromethylation

A simple copper-promoted one-pot Sandmeyer trifluoromethylation of aromatic amines with Langlois’ reagent has been demonstrated. The reaction is performed in mild reaction conditions under an air atmosphere with good substrate scope and functional group compatibility. It provides an alternative and straightforward synthetic approach to access a variety of trifluoromethylated arenes.

Synthesis method of trifluperidol drug intermediate m-bromobenzotrifluoride

The invention relates to a synthesis method of a trifluperidol drug intermediate m-bromobenzotrifluoride, which comprises the following steps: (i) adding 300mL of 50-70 wt% potassium chloride solution into a reaction vessel which is provided with a stirrer, a thermometer and a dropping funnel, control the stirring rate at 300-500 rpm, adding 0.35mol of m-aminobromobenzotrifluoride (2), heating the solution to 60-65 DEG C until the solid is completely dissolved, cooling to 5-8 DEG C, dropwisely adding 0.35-0.39mol of sodium nitrate in 60ml of water to prepare a solution, controlling the reaction temperature at 15-20 DEG C, and determining the end point with potassium iodide test paper to obtain diazonium salt (3); and (ii) adding 0.12 mol of nickel dichloride into 300ml of sodium bromide solution, heating the solution to 85-90 DEG C, adding the diazonium salt (3) solution obtained in the step (i), carrying out steam distillation until no organic matters are distilled out, separating out the organic layer, washing with a solution, washing with a salt solution, washing with a neutralizing solution, dehydrating with a dehydrating agent, distilling under reduced pressure, and collecting the 80-85-DEG C fraction to obtain the m-bromobenzotrifluoride.

Copper-Promoted Trifluoromethanesulfonylation and Trifluoromethylation of Arenediazonium Tetrafluoroborates with NaSO2CF3

A tunable chemoselective trifluoromethanesulfonylation and trifluoromethylation of arenediazonium tetrafluoroborates with Langlois' reagent (NaSO2CF3) was developed. The Cu2O-catalyzed reaction in DMSO gave aryl trifluoromethanesulfones as the major products. On the other hand, the trifluoromethylated arenes were produced in the presence of oxidant tert-butyl hydroperoxide, CuBF4(MeCN)4, and 2,2′;6′,2 terpyridine (tpy). Both of these transformations proceed under mild conditions and tolerate functional groups.

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.

Tribromoisocyanuric acid in trifluoroacetic acid: An efficient system for smooth brominating of moderately deactivated arenes

Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48-85% isolated yield. This medium avoids the polybromination of the substrate, observed in the same reaction performed in 98% H 2SO4. Georg Thieme Verlag Stuttgart · New York.

Silver catalyzed bromination of aromatics with N-bromosuccinimide

A heterogeneous silver catalyst was prepared and applied efficiently for the selective bromination of aromatics with NBS. The silver nanoparticles combined with the acidic support HMB can activate both the aromatic ring and NBS, and the synergistic effects between the silver nanoparticles and the HMB highly enhanced the efficiency of the bromination reaction.