345-40-4

Usage

Class

Organofluorine compounds

Structure

Phenyl ring and five fluorine atoms attached to a propanol moiety

Usage

Solvent in chemical reactions and processes, reagent in organic synthesis, forms stable and selective complexes with metal ions for use in analytical chemistry and separation techniques, synthesis of drugs in pharmaceutical industry, and intermediate in production of agrochemicals

Safety

Potentially hazardous, requires careful handling and appropriate safety measures

Upstream product

• 422-06-0 2,2,3,3,3-Pentafluoro-propionaldehyde 
• 394-52-5 pentafluoroethyl phenyl ketone 
• 354-64-3 Pentafluoroethyl iodide 
• 100-52-7 benzaldehyde 
• 124898-13-1 trimethyl(pentafluoroethyl)silane 
• 91935-83-0 (Pentafluoroethyl)lithium 
• 378-75-6 perfluoropropionic acid methyl ester 
• 591-51-5 phenyllithium 
• 354-33-6 1,1,1,2,2-pentafluoroethane 
• 865-47-4 potassium tert-butylate 
• 426-65-3 ethyl Pentafluoropropionate 
• 867212-85-9 C₉H₉F₁₅NPSi 
• 14856-93-0 pentafluoroethyl phenyl sulfone 

Downstream Products

• 131510-37-7 1,2,2,3,3,3-hexafluoro-1-phenyl-propane 
• 884855-23-6 1-chloro-1-phenyl-2,2,3,3,3-pentafluoropropane 
• 394-52-5 pentafluoroethyl phenyl ketone 
• 41424-70-8 (Z)-1-phenyl-1,2,3,3,3-pentafluoro-1-propene 
• 78693-66-0 2,2,3,3,3-pentafluoro-1-phenylpropane 
• 41500-48-5 (E)-1-phenyl-1,2,3,3,3-pentafluoro-1-propene 
• 78693-68-2 Toluene-4-sulfonic acid 2,2,3,3,3-pentafluoro-1-phenyl-propyl ester 

Relevant academic research and scientific papers

Pentafluoroethyl group containing production of alcohols, organic semiconductor material and intermediate compound of the enzyme activity inhibitor

[A] a pharmaceutical, agrochemical, a pentafluoroethyl group containing alcohol compound useful as a method for producing polymeric functional materials, as well as, organic semiconductor material and enzyme activity inhibitor of the intermediate compound

Pentafluoroethylation of Carbonyl Compounds Using HFC-125 in a Flow Microreactor System

The protocol of micro-flow nucleophilic pentafluoroethylation using pentafluoroethane (HC2F5, HFC-125), a nontoxic, inexpensive, and commercially available greenhouse gas, is described. The micro-flow pentafluoroethylation by HFC-125 proceeded smoothly at

Pentafluoroethylation of Carbonyl Compounds by HFC-125 via the Encapsulation of the K Cation with Glymes

A simple protocol to overcome the explosive pentafluoroethylation of carbonyl compounds by HFC-125 is described. The use of potassium (K) bases with triglyme or tetraglyme as a solvent safely yields the pentafluoroethylation products in good to high yield

Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands

The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2-trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2-phenyl-3-(haloacetyl)-indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.

On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)5]?, and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5

Pentafluoroethyllithium, LiC2F5, has been established as an efficient and versatile reagent for the transfer of the pentafluoroethyl unit to a number of electrophiles. Here, the stability of this species up to ?40 °C is of advantage, particularly in comparison to its smaller congener LiCF3. The usual production of LiC2F5, however, from gaseous HC2F5 or IC2F5 and strong bases requires specially designed apparatuses, which severely impeded its value as a laboratory reagent. In this contribution we communicate an alternative gas-free and highly efficient protocol for the synthesis of LiC2F5 from the already commercialized stannate salt [PPh4][Sn(C2F5)5]. The [Sn(C2F5)5]? anion represents not only the first example of a structurally characterized hypervalent pentaalkylstannate but also serves as a precursor for the synthesis of the homoleptic tetrakis(pentafluoroethyl)stannane, Sn(C2F5)4. The reaction of the latter with n-butyllithium provides an insight into the mechanism of LiC2F5 generation.

Method for Producing Fluorine-Containing Substituted Compound and Fluorine-Containing Substituted Compound

A method for producing a fluorine-containing substituted compound, the method including: introducing an organofluorine compound and an organolithium compound into a microreactor provided with a flow path capable of mixing a plurality of liquids, to thereby obtain a reaction product; and introducing, into the microreactor, the reaction product and an electrophile exhibiting electrophilic effect on the reaction product, to thereby obtain a fluorine-containing substituted compound.

Perfluoroalkylation in flow microreactors: Generation of perfluoroalkyllithiums in the presence and absence of electrophiles

Perfluoroalkyllithiums were effectively generated from perfluoroalkyl halides in the presence and absence of electrophiles using flow microreactor systems. The in situ trapping with electrophile is conducted at much higher temperatures than those required for batch macro reactors. The subsequent trapping method is quite effective for highly reactive electrophiles that are not compatible with the lithiation process.

Nucleophilic trifluoromethylation with organoboron reagents

Potassium trialkoxy(trifluoromethyl)borates are shown to behave as convenient reagents for nucleophilic trifluoromethylation of non-enolizable aldehydes and N-tosylimines to give CF3-substituted alcohols and N-tosylamines in good yields.

Nucleophilic perfluoroalkylation of imines and carbonyls: Perfluoroalkyl sulfones as efficient perfluoroalkyl-transfer motifs

Alkoxide-induced nucleophilic pentafluoroethylation and trifluoromethylation of aldehydes, ketones, and imines using pentafluoroethyl phenyl sulfone (PhSO2CF2CF3, 1) and trifluoromethyl phenyl sulfone (PhSO2CF3, 2), respectively, have been successfully achieved. High diastereoselectivity was observed during the perfluoroalkylation of homochiral sulfinimines to give the corresponding perfluoroalkyl sulfinamides.

Electrochemical fluorination (Simons process) - A powerful tool for the preparation of new conducting salts, ionic liquids and strong Br?nsted acids

Electrochemical fluorination (Simons process) provides a cheap commercial access to a series of tris(perfluoroalkyl)diflurophosphoranes. These substances are convenient starting material for the preparation of various fluoro-chemicals. The synthesis of ne