655-26-5

Usage

InChI:InChI=1/C8H4BrF3O/c9-6-3-1-2-5(4-6)7(13)8(10,11)12/h1-4H

Upstream product

• 434-45-7 2,2,2-Trifluoroacetophenone 
• 111762-31-3 3-bromophenyl magnesium bromide 
• 407-25-0 trifluoroacetic anhydride 
• 446-63-9 (±)-1-(3-bromophenyl)-2,2,2-trifluoroethanol 
• 618-89-3 methyl 3-bromobenzoate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 207681-67-2 N-methoxy-N-methyl-3-bromobenzamide 
• 3132-99-8 m-bromobenzoic aldehyde 
• 383-63-1 ethyl trifluoroacetate, 
• 108-36-1 1,3-dibromobenzene 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 75-46-7 trifluoromethan 
• 24398-88-7 ethyl 3-bromobenzoate 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 

Downstream Products

• 122243-31-6 3-(2,2,2-Trifluoro-1-hydroxy-1-methyl-ethyl)-benzonitrile 
• 122242-97-1 Toluene-4-sulfonic acid 1-(3-bromo-phenyl)-2,2,2-trifluoro-1-methyl-ethyl ester 
• 122243-13-4 3-Nitro-benzenesulfonic acid 1-(3-bromo-phenyl)-2,2,2-trifluoro-1-methyl-ethyl ester 
• 122243-15-6 3-Nitro-benzenesulfonic acid 1-(3-cyano-phenyl)-2,2,2-trifluoro-1-methyl-ethyl ester 
• 1566469-95-1 (E)-1-bromo-3-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene 
• 1566469-97-3 (Z)-1-bromo-3-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene 
• 1448318-87-3 3-(1,1,1-trifluoro-2-methylpropan-2-yl)benzoic acid 
• 1448318-86-2 1-bromo-3-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene 
• 1448318-85-1 2-(3-bromophenyl)-1,1,1-trifluoropropan-2-yl-methanesulphonate 
• 1402403-26-2 C₁₉H₁₄BrF₃O₃ 
• 1402403-35-3 C₁₈H₁₂F₃N₃O₃ 
• 1402403-34-2 C₁₂H₉F₃O₃ 
• 142719-80-0 1-(3-bromophenyl)-2,2,2-trifluoro-1-ethanone O-(p-tolylsulfonyl)oxime 
• 142992-88-9 2,3-dihydroxy-3-(3-<3-(trifluoromethyl)diazirin-3-yl>phenyl)propionic acid 

Relevant academic research and scientific papers

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

A straightforward method that enables the formation of biologically attractive trifluoromethyl ketones from readily available methyl esters using the potent greenhouse gas fluoroform (HCF3, HFC-23) was developed. The combination of fluoroform and KHMDS in triglyme at ?40 °C was effective for this transformation, with good yields as high as 92%. Substrate scope of the trifluoromethylation procedure was explored for aromatic, aliphatic, and conjugated methyl esters. This study presents a straightforward trifluoromethylation process of various methyl esters that convert well to the corresponding trifluoromethyl ketones. The tolerance of various pharmacophores under the reaction conditions was also explored.

One-Pot Successive Turbo Grignard Reactions for the Facile Synthesis of α-Aryl-α-Trifluoromethyl Alcohols

A novel straightforward one-pot methodology for two successive turbo Grignard reagent (iPrMgCl·LiCl) reactions, was developed for a facile synthesis of α-aryl-α-trifluoromethyl alcohols, motifs of value in pharmaceutical chemistry. The method displayed broad functional group tolerance, including reducible groups. Dual roles of iPrMgCl·LiCl were exploited in the tandem reaction with commercially available iodoarenes or iodoheteroarenes and 2,2,2-trifluoroethyl trifluoroacetate. The process encompasses three successive reactions in a one-pot process: the iPrMgCl·LiCl-mediated iodine/magnesium-exchange reaction of iodoarenes or iodoheteroarenes; nucleophilic addition of various generated aryl or heteroarylmagnesium reagents to 2,2,2-trifluoroethyl trifluoroacetate; and the reduction of in-situ generated aryl trifluoromethyl ketones with iPrMgCl·LiCl, to produce the corresponding α-aryl or α-heteroaryl-α-trifluoromethyl alcohols bearing various substituents, including reducible functional groups in good to excellent yields.

Fluoroform: an Efficient Precursor for the Trifluoromethylation of Aromatic Esters by Sodium Diisopropylamide with Trialkylamines

The trifluoromethanide anion is the postulated key intermediate in nucleophilic trifluoromethylation reactions. It is believed to be incompatible with Na+ cation due to the strong Na–F bond. However, herein we demonstrate that it could be prepared for the first time. Trialkylamines can be used as cation chelating agents to stabilize the isolated –CF3 ion to realize trifluoromethylation reaction. With this strategy, trifluoromethyl aromatic ketones could be effectively synthesized from fluoroform and aromatic esters with diisopropyl aminosodium (NaDA) and trialkylamines.

Copper-Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate

A copper-mediated trifluoroacetylation of various arenediazonium salts with ethyl trifluoropyruvate is reported. The reaction proceeded smoothly under mild conditions at room temperature giving trifluoromethyl aryl ketones in moderate to good yields. A variety of functional groups, including methoxy, hydroxy, ester, ketone, trifluoromethyl, and halide groups, were well tolerated. A possible reaction mechanism involving an aryl radical intermediate was proposed and supported by experimental evidence. This reaction provides a new route to trifluoromethyl aryl ketones, notable synthetic targets, from the corresponding anilines.

Fluorescent Recognition of 1,2-Diamines by a 1,1′-Binaphthyl-Based Trifluoromethyl Ketone

The fluorescent responses of a 1,1′-binaphthol (BINOL)-based trifluoromethyl aryl ketone toward a variety of amines have been studied. The aliphatic 1,2-diamines, especially ethylenediamine, can greatly enhance the fluorescence of this compound, but under

One-pot multistep synthesis of trisubstituted alkenes from N -tosylhydrazones and alcohols

A one-pot procedure for the synthesis of trisubstituted alkenes from N-tosylhydrazones and alcohols is reported. This procedure combines the aerobic oxidation reaction and Wittig reaction in one pot, which avoids using of environmentally toxic oxidants and isolation of the intermediates. The simple procedure makes it very attractive for the synthesis of trisubstituted alkenes when alcohols are used as starting materials. A variety of trisubstituted alkenes as well as trifluoromethyl-substituted alkenes were obtained in moderate to good yields (up to 84%) with good E-selectivity (up to 99%). Georg Thieme Verlag Stuttgart.New York.

Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX)

A two-step process for the synthesis of aryl and heteroaryl trifluoromethyl ketones from the corresponding aldehydes is described. Trifluoromethyl alcohols were prepared from aryl and heteroaryl aldehydes in excellent yields using catalytic amount of K2CO3. The trifluoromethyl alcohols were then oxidized conveniently and efficiently by o-iodoxybenzoic acid (IBX) under mild conditions to get the desired functionalized aryl and heteroaryl trifluoromethyl ketones.

A Weinreb amide approach to the synthesis of trifluoromethylketones

A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.

Novel thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions

Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula I or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.

NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS

Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula (I) or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.