13541-18-9

Usage

Uses

Used in Organic Synthesis:
1-(4-bromophenyl)-3,3,3-trifluoropropan-1-one is used as a reagent in organic synthesis for its versatile intermediate properties, allowing for the creation of various pharmaceuticals and agrochemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(4-bromophenyl)-3,3,3-trifluoropropan-1-one is used as a key intermediate in the development of new drugs, contributing to the advancement of medical treatments.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, 1-(4-bromophenyl)-3,3,3-trifluoropropan-1-one serves as an essential intermediate for the synthesis of various products, playing a crucial role in the development of agricultural chemicals to improve crop protection and yield.

Upstream product

• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 887144-94-7 Togni's reagent II 
• 25294-65-9 3-(4-bromophenyl)-2-propynoic acid 
• 342808-62-2 1-(4-bromophenyl)vinyl acetate 
• 2926-29-6 Langlois reagent 
• 99-90-1 para-bromoacetophenone 
• 122948-58-7 1-(4-bromophenyl)vinyl trifluoromethanesulfonate 
• 73387-60-7 1-(4-bromophenyl)-3-(dimethylamino)prop-2-en-1-one 
• 108-86-1 bromobenzene 
• 41463-83-6 3,3,3-trifluoropropanoyl chloride 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 7119-09-7 1-bromo-4-(3,3,3-trifluoro-1-propyn-1-yl)benzene 
• 55991-66-7 1-(4-bromophenyl)-1-(trimethylsilyloxy)ethylene 
• 407-25-0 trifluoroacetic anhydride 

Relevant academic research and scientific papers

Rational Design and Development of Low-Price, Scalable, Shelf-Stable and Broadly Applicable Electrophilic Sulfonium Ylide-Based Trifluoromethylating Reagents

The development of two highly reactive electrophilic trifluoromethylating reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as a trifluoromethyl radical for a variety of trifluoromethylative transformations under visible light irradiation, including radical trifluoromethylation of electron-rich indoles and pyrroles and sodium aryl sulfinates as well as trifluoromethylative difunctionalization with styrene derivatives. On the other hand, as a complimentary, under reductive coupling conditions, reagent 1j reacted with a variety of (hetero)aryl iodides for the formation of trifluoromethylated (hetero)arenes.

Scissoring Enaminone C=C Double Bond by Free Radical Process for the Synthesis of α-Trifluoromethyl Ketones with CF3SO2Na

The C=C double bond cleavage on tertiary enaminones, enabling the formation of a new C-CF3 bond, has been realized as a practical method for the synthesis of α-trifluoromethyl ketones with only the promotion of TBHP and ambient heating. Control experiments support that the reactions proceed via a featured free radical process. The deuterium labeling experiment employing D2O indicates that water participated in the product formation by donating the hydrogen atom for the newly generated α-C-H bond in the product.

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

The electrochemical synthesis of fluorinated ketones from enol acetates and RfSO2Na in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded via perfluoroalkyl radical generation from sodium perfluoroalkyl sulfinate followed by addition to the enol acetate and transformation of the resulting C radical to a fluorinated ketone. The method is applicable to a wide range of enol acetates and results in the desired products in yields of 20 to 85%.

METHOD FOR PRODUCING α-FLUOROALKYL KETONE AND β-FLUOROALKYL ALCOHOL

PROBLEM TO BE SOLVED: To provide a method for producing α-fluoroalkyl ketone and β-fluoroalkyl alcohol conveniently, inexpensively and efficiently. SOLUTION: A method for producing α-fluoroalkyl ketone represented by formula (II) (where Rf is a fluoroalkyl group) includes reacting an alkyne compound represented by formula (I) (where R1 is a chain hydrocarbon group, cyclic aliphatic hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, -OR3, -NR4R4', R2 is a hydrogen atom, trialkylsilyl group, diallyl alkylsilyl group, or triallylsilyl group), in the presence of a radical initiator, with a fluoroalkyl sulfonic acid. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide

Most photoredox catalysts in current use are precious metal complexes or synthetically elaborate organic dyes, the cost of which can impede their application for large-scale industrial processes. We found that a combination of triphenylphosphine and sodium iodide under 456-nanometer irradiation by blue light–emitting diodes can catalyze the alkylation of silyl enol ethers by decarboxylative coupling with redox-active esters in the absence of transition metals. Deaminative alkylation using Katritzky’s N-alkylpyridinium salts and trifluoromethylation using Togni’s reagent are also demonstrated. Moreover, the phosphine/iodide-based photoredox system catalyzes Minisci-type alkylation of N-heterocycles and can operate in tandem with chiral phosphoric acids to achieve high enantioselectivity in this reaction.

Direct Photoassisted α-Trifluoromethylation of Aromatic Ketones with Trifluoroacetic Anhydride (TFAA)

Direct α-Trifluoromethylation of acetophenone derivatives was achieved by using trifluoroacetic anhydride (TFAA) as the trifluoromethyl source and pyridine-N-oxide (Py?O) as activator and oxidant under visible light irradiation and tris-(2,2′-bipyridine)ruthenium(II) hexafluorophosphate (Ru(bpy)3(PF6)2) as the photocatalyst. Different acetophenone derivatives could be converted to the corresponding α-CF3 derivatives with high selectivity. Extensive mechanistic investigation revealed the formation of vinyl trifluoroacetate as the key intermediate for this transformation. (Figure presented.).

On the reactivity of anodically generated trifluoromethyl radicals toward aryl alkynes in organic/aqueous media

An in-depth study of the reaction of electrochemically generated trifluoromethyl radicals with aryl alkynes in the presence of water is presented. The radicals are readily generated by anodic oxidation of sodium triflinate, an inexpensive and readily avai

Visible light induced Trifluoromethyl Migration: Easy Access to α-Trifluoromethylated Ketones from Enol Triflates

Herein, we reported a novel method to synthesize α-trifluoromethylated ketones from enol triflates. Involving a cascade sulfur dioxide extrusion and a CF3 (trifluoromethyl) radical addition process, this reaction proceeds at room temperature an

Photooxidative Keto-Trifluoromethylation of Styrenes by Means of an Anthraquinone-Based Organocatalyst

α-Trifluoromethyl ketones are versatile building blocks for the synthesis of various trifluoromethyl-functionalized molecules. Although there are significant advantages in the development of methods toward direct transformations of styrenes into α-trifluoromethyl ketones, most procedures leading to α-trifluoromethyl ketones require heavy- or transition-metal-based complexes. Herein, a novel method is developed for the synthesis of α-trifluoromethyl ketones via anthraquinone-catalyzed photooxidative keto-trifluoromethylation of styrenes with the readily available Langlois reagent (CF 3 SO 2 Na) under an oxygen atmosphere. The reactions proceed smoothly to give the products in moderate to excellent yield with good selectivity.