2369-31-5

Usage

Uses

Used in Pharmaceutical Industry:
4'-Phenyl-2,2,2-trifluoroacetophenone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to enhance the biological activity of the final compounds. Its unique trifluoromethyl group and carbonyl functionality allow for the development of new drugs with improved pharmacokinetic and pharmacodynamic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 4'-Phenyl-2,2,2-trifluoroacetophenone is employed as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can lead to enhanced efficacy and selectivity in controlling pests and weeds, thereby improving crop yields and quality.
Used in Organic Synthesis:
4'-Phenyl-2,2,2-trifluoroacetophenone is used as a building block in organic synthesis for the creation of a wide range of biologically active compounds. Its versatile reactivity and functional group compatibility make it an ideal candidate for the development of new organic molecules with potential applications in various fields, such as medicine, materials science, and chemical research.
Used as a Reagent in Organic Chemistry:
In organic chemistry, 4'-Phenyl-2,2,2-trifluoroacetophenone serves as a reagent in the preparation of diverse organic compounds. Its unique properties facilitate various synthetic reactions, enabling the synthesis of complex organic molecules with specific functionalities and structures. This makes it a valuable tool for researchers and chemists working in the field of organic chemistry.

InChI:InChI=1/C14H9F3O/c15-14(16,17)13(18)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H

Upstream product

• 92-66-0 4-bromo-1,1'-biphenyl 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2714-87-6 [1,1′-biphenyl]-4-carbonyl fluoride 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 1591-31-7 4-iodo-biphenyl 

Downstream Products

• 123492-57-9 C₂₁H₁₆F₃NO₃S 
• 1160936-91-3 2,2,2-trifluoro-1-(1H-indole-3-yl)-1-(4-biphenyl)ethanol 
• 1369922-82-6 phenyl 3-(biphenyl-4-yl)-4,4,4-trifluoro-3-hydroxybutanoate 

Relevant academic research and scientific papers

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.

Stoichiometric Studies on the Carbonylative Trifluoromethylation of Aryl Pd(II) Complexes using TMSCF3 as the Trifluoromethyl Source

We have performed a series of stoichiometric studies in order to identify viable steps for a hypothetical catalytic cycle for the palladium-mediated carbonylative coupling of an aryl bromide with TMSCF3. Our work revealed that benzoyl Pd(II) complexes bearing Xantphos or tBu3P as the phosphine ligands, which are generated from the corresponding PdII(Ph)Br complexes exposed to stoichiometric 13CO from 13COgen, were unable to undergo transmetalation and reductive elimination to trifluoroacetophenone. Instead, in the presence of base and additional CO, these organometallic complexes readily underwent reductive elimination to the acid fluoride. Attempts to determine whether the acid fluoride could represent an intermediate for acetophenone production were unrewarding. Only in the presence of a boronic ester did we observe some formation of the desired product, although the efficiency of transformation was still low. Finally, we investigated the reactivity of four phosphine-ligated PdII(Ph)CF3 complexes (Xantphos, DtBPF, tBu3P, and triphenylphosphine) with carbon monoxide. With the exception of the tBu3P-ligated complex, all other metal complexes led to the facile formation of trifluoroacetophenone. We also determined in the case of triphenylphosphine that CO insertion occurred into the Pd-Ar bond, as trapping of this complex with n-hexylamine led to the formation of n-hexylbenzamide.