394-52-5

Usage

Uses

Used in Pharmaceutical Industry:
Pentafluoroethyl Phenyl Ketone is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique structure, which includes fluorine atoms and a ketone functional group, allows it to be a valuable building block in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, Pentafluoroethyl Phenyl Ketone is used as a reagent or a precursor in the preparation of complex organic molecules. Its fluorinated nature and ketone functionality make it a versatile component in the synthesis of a wide range of compounds.
Used in Chemical Research:
Pentafluoroethyl Phenyl Ketone is also used in chemical research as a model compound to study the effects of fluorination on the properties and reactivity of aryl and aralkyl ketones. This can provide insights into the development of new synthetic methods and the design of novel compounds with improved properties.

Upstream product

• 422-64-0 pentafluoropropionic acid 
• 422-59-3 2,2,3,3,3-pentafluoropropionyl chloride 
• 378-75-6 perfluoropropionic acid methyl ester 
• 591-51-5 phenyllithium 
• 426-65-3 ethyl Pentafluoropropionate 
• 71-43-2 benzene 
• 93-58-3 benzoic acid methyl ester 
• 116-14-3 polytetrafluoroethylene 
• 455-32-3 benzoyl fluoride 
• 887144-97-0 Togni's reagent 
• 86340-78-5 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene 
• 887144-94-7 Togni's reagent II 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 108-86-1 bromobenzene 

Downstream Products

• 345-40-4 2,2,3,3,3-Pentafluoro-1-phenyl-propan-1-ol 
• 1265324-75-1 2-fluoro-2-(trifluoromethyl)-1-phenylhexane-1,5-dione 
• 1214364-82-5 6-(trifluoromethyl)biphenyl-3-ol 
• 774-65-2 benzoic acid tert-butyl ester 
• 2823-51-0 1,1,1,2,2,4,4,5,5,5-decafluoro-3-hydroxy-3-phenylpentane 
• 1353741-50-0 (S)-5,5,6,6,6-pentafluoro-4-hydroxy-4-phenyl-hexan-2-one 
• 101417-69-0 3-hydroxy-1,1,1,2,2-pentafluoro-3-phenylbutane 
• 143888-60-2 1-(pentafluoroethyl)-1-phenylethyl tosylate 
• 5300-25-4 2-phenylperfluorobutene-1 
• 74031-42-8 (3,3,3-trifluoroprop-1-enyl)benzene 
• 1579-80-2 (3,3,3-trifluoropropyl)benzene 
• 24165-19-3 {1-[1-Chloro-1-fluoro-meth-(Z)-ylidene]-2,2,3,3,3-pentafluoro-propyl}-benzene 
• 24165-18-2 {1-[1-Chloro-1-fluoro-meth-(E)-ylidene]-2,2,3,3,3-pentafluoro-propyl}-benzene 

Relevant academic research and scientific papers

CsF-Catalyzed Fluoroacylation of Tetrafluoroethylene Using Acyl Fluorides for the Synthesis of Pentafluoroethyl Ketones

A catalytic method for the synthesis of pentafluoroethyl ketones has been developed. The cesium fluoride catalyst can be used to convert acyl fluorides into the pentafluoroethyl ketones under tetrafluoroethylene pressure without generating stoichiometric

Trifluoromethylthiolation, Trifluoromethylation, and Arylation Reactions of Difluoro Enol Silyl Ethers

This study reports a new application area of difluoro enol silyl ethers, which can be easily obtained from trifluoromethyl ketones. The main focus has been directed to the electrophilic fluoroalkylation and arylation methods. The trifluoromethylthiolation of difluoro enol silyl ethers can be used for the construction of a novel trifluoromethylthio-α,α-difluoroketone (-COCF2SCF3) functionality. The -CF2SCF3 moiety has interesting properties due to the electron-withdrawing, albeit lipophilic, character of the SCF3 group, which can be combined with the high electrophilicity of the difluoroketone motif. The methodology could also be extended to difluoro homologation of the trifluoromethyl ketones using the Togni reagent. In addition, we presented a method for transition-metal-free arylation of difluoro enol silyl ethers based on hypervalent iodines.

Well-defined CuC2F5 complexes and pentafluoroethylation of acid chlorides

Four new well-defined CuI complexes bearing a C2F5 ligand have been prepared and fully characterized: [(Ph3P)2CuC2F5] (2), [(bpy)CuC2F5] (3), [(Ph3P)Cu(phen)C2F5] (4), and [(IPr)CuC2F5] (5). X-ray structures of all four have been determined, showing that the C2F5-ligated Cu atom can be di- (5), tri- (2 and 3), and tetracoordinate (4). The mixed phen-PPh3 complex 4 is a highly efficient fluoroalkylating agent for a broad variety of acid chlorides. This high-yielding transformation represents the first general method for the synthesis of RCOC2F5 from the corresponding RCOCl. Four well-defined CuC2F5 complexes have been prepared and fully characterized, with [(phen)Cu(PPh3)C2F5] (phen=1,10-phenanthroline) proving to be a remarkably efficient fluoroalkylating agent for a broad variety of acid chlorides (see scheme). The procedure represents the first general method for the one-step conversion of RCOCl into valuable pentafluoroethyl ketones.

Enantioselective NHC-Catalyzed Redox [2+2] Cycloadditions with Perfluoroketones: A Route to Fluorinated Oxetanes

The N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.

A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation

Oxidation of various fluoroalkyl-substituted methanol derivatives under the influence of a catalytic amount of sodium 2-iodobenzenesulfonate and Oxone in CH3CN or CH3NO2 was investigated in detail. The efficiency of the newly developed oxidation was also evaluated by comparison to other oxidations, such as Dess-Martin, PDC, and Swern oxidation.

Synthesis of trifluoromethyl cyclohexyl, cyclohexenyl and aryl compounds via stepwise Robinson annulation

The diketone 2-fluoro-2-(trifluoromethyl)-1-phenylhexane-1,5-dione 3 was synthesized by a Mukaiyama Michael type reaction from the corresponding tetrafluoroenol silyl ether prepared from pentafluoropropiophenone. This diketone was treated under basic cond

Unusual reactions of Grignard reagents toward fluoroalkylated esters

Fluorine-containing esters were demonstrated to be convenient substrates for construction of the corresponding ketones by low temperature reaction with Grignard reagents followed by warming up to 0 °C, while heating the mixture up to 80 °C readily promoted the reduction of the ketones obtained by the generated magnesium alkoxides whose mechanism was speculated as Meerwein-Ponndorf-Verley type reduction by computational technique.

A simple procedure for nucleophilic perfluoroalkylation of organic and inorganic substrates

The mixture RfI and tetrakis(dimethylamino)ethylene is used for the nucleophilic perfluoroalkylation. The reaction of chlorotrimethylsilane and RfI/tetrakis(dimethylamino)ethylene in diglyme results in the formation of RfSi(CH3)3 isolated in 55-81% yield. The interaction of this system with organic electrophiles such as benzoyl and benzensulphonyl chlorides, aliphatic and aromatic aldehydes and activated ketones leads to the formation of the corresponding condensation products in 24-62% yield.

Chiral Synthesis Via Organoboranes. 38 Selective Reductions. 48. Asymmetric Reduction of Trifluoromethyl Ketones by B-Chlorodiisopinocampheylborane in High Enantiomeric Purity

(-)-B-Chlorodiisopinocampheylborane TM,1>, introduced by us several years ago, has been shown to reduce prochiral aryl and alkyl perfluorinated ketones to the corresponding optically active alcohols in very high ee.For example, 2,2,2-trifluoroacetophenone, trifluoroacetyl-1-naphthalene, and trifluoroacetyl-2-naphthalene are all reduced with 1 within 1-3 d at rt in 90percent ee, 78percent ee and 91percent ee, respectively.The optical purity of 1-phenyl-2,2,2-trifluoroethanol is upgraded to = 99percent ee by crystallizing the initially formed products from pentane. 1,1,2,2,2- pentafluoropropiophenone and 1,1,2,2,3,3,3-heptafluorobutyrophenone are reduced in 3 d with 1 to the corresponding alcohols in 92percent ee and 87 percent ee, respectively.The reagent reduces alkyl trifluoromethyl ketones at a rate faster than that of the aryl derivatives, while still providing the product alcohols in very high ee.Thus, 1,1,1-trifluoroacetone, 1,1,1-trifluorononan-2-one, and 1,1,1-trifluorodecan-2-one are all reduced within 4 - 8 h in 89percent ee, 92percent ee, and 91percent ee, respectively.Even α-sec-alkyl trifluoromethyl ketones are handled by 1 very efficiently.Thus cyclohexyl trifluoromethyl ketone is reduced by 1 at rt in 12 h to the product alcohol in 87percent ee.In all of these cases the trifluoromethyl group acts as the enantiocontrolling larger group as compared to the aryl or alkyl group.This produces alcohol products with stereochemistry opposite to those obtained for the corresponding hydrogen analogs.The steric and electronic influence of the trifluoromethyl group in achieving enantiocontrol in assymmetric reductions is discussed.Keywords: asymmetric reduction; trifluoromethyl ketones; DIP-Chloride; high enantiomeric purity

Esters of arylbisperfluoroalkylcarbinols, and a process for the preparation of these compounds

The invention relates to esters of the general formula IV STR1 wherein R1 to R5 represent at least one of the substituents hydrogen, halogen, alkyl, alkoxy, alkylthio and perfluorinated alkyl, each having from 1 to 6 carbon atoms and