17556-44-4

Usage

Uses

Used in Organic Synthesis:
2,2,2-Trifluoro-1-(naphthalen-1-yl)ethanol is used as a building block in the preparation of various pharmaceuticals and agrochemicals. Its unique structure allows for the development of new compounds with specific therapeutic or pesticidal properties.
Used as a Solvent in Chemical Reactions:
Due to its fluorinated nature, 2,2,2-trifluoro-1-(naphthalen-1-yl)ethanol can be employed as a solvent in chemical reactions. Its ability to dissolve a wide range of compounds and facilitate specific reaction pathways makes it a valuable asset in the synthesis of complex organic molecules.
Used as a Reagent in the Synthesis of Fluorinated Compounds:
The presence of fluorine atoms in 2,2,2-trifluoro-1-(naphthalen-1-yl)ethanol makes it an effective reagent for the synthesis of other fluorinated compounds. Its fluoro-substituted structure can be utilized to introduce fluorine-containing functionalities into target molecules, which can enhance their properties and applications.
Used in Research and Development of New Materials:
The unique structure and properties of 2,2,2-trifluoro-1-(naphthalen-1-yl)ethanol make it an interesting candidate for further research in the development of new materials and pharmaceuticals. Its potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science, warrant continued investigation and exploration.

Upstream product

• 6500-37-4 2,2,2-trifluoro-1-(naphthalen-1-yl)ethanone 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 90-11-9 1-Bromonaphthalene 
• 66-77-3 1-naphthaldehyde 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2314-97-8 iodotrifluoromethane 
• 426-58-4 (trifluoromethylsulfonyl)benzene 
• 703-55-9 1-naphthylmagnesiumbromide 
• 75-46-7 trifluoromethan 
• 340-07-8 N-(trifluoroacetyl)piperidine 
• 4780-79-4 1-naphthalene methanol 
• 185739-16-6 1-(2,2-difluoro-ethenyl)naphthalene 
• 90-14-2 1-Iodonaphthalene 
• 844-40-6 diphenylmethanol trifluoroacetate 

Downstream Products

• 6500-37-4 2,2,2-trifluoro-1-(naphthalen-1-yl)ethanone 

Relevant academic research and scientific papers

Direct preparation of trifluoromethylindium reagents from trifluoromethyl iodide: Effective trifluoromethylation and perfluoroalkylation reagents

The direct synthesis of trifluoromethylindium reagents prepared from trifluoromethyl iodide by using just one equivalent each of indium, lithium chloride or sodium iodide, and ferrocene is reported. The weak In···F interaction is suitable to prepare stable but nucleophilic perfluoroalkyl reagents, which were successfully employed in the perfluoroalkylation of aldehydes. Notably, the nucleophilic trifluoromethylation of various aldehydes took place with trifluoromethyl iodide by utilizing just one equivalent each of indium, lithium chloride, and ferrocene.

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.

One-Pot and Reducible-Functional-Group-Tolerant Synthesis of α-Aryl- and α-Heteroaryl-α-Trifluoromethyl Alcohols via Tandem Trifluoroacetylation and MPV Type Reduction

We have developed a new one-pot synthesis of α-aryl- and α-heteroaryl-α-trifluoromethyl alcohols carrying not only arenes with electron-withdrawing groups but also electron-deficient nitrogen-containing heteroarenes, which are of increasing interest becau

Palladium-Catalyzed Direct Approach to α-Trifluoromethyl Alcohols by Selective Hydroxylfluorination of gem-Difluoroalkenes

A novel palladium-catalyzed selective hydroxylfluorination of gem-difluoroalkenes has been developed. By employing easily obtainable gem-difluoroalkenes and NFSI as the fluorine source, the scope, advantages, and limitations of this reaction were investigated. The reaction presents an efficient synthesis to afford a series of α-trifluoromethyl alcohols in good to excellent yields. Furthermore, this reaction probably proceeds via oxidation of Pd0 to PdII fluoride complex by NFSI, followed by fluoropalladation of gem-difluoroalkenes to generate an α-trifluoromethylbenzyl–Pd intermediate. And this strategy offers more possibilities for the construction of other bonds, such as C–C, C–N and C–S.

Oxidation of α-trifluoromethyl and non-fluorinated alcohols: Via the merger of oxoammonium cations and photoredox catalysis

We present an alcohol oxidation strategy to access α-trifluoromethyl ketones (TFMKs) merging catalytic oxoammonium cation oxidation with visible-light photoredox catalysis. This work uses 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl as an organic oxidant capable of generating TFMKs in good yields. The methodology serves as an improvement over previous reports of an analogous oxidation strategy requiring superstoichiometric quantities of oxidant. Both primary and secondary non-fluorinated alcohols can also be oxidised in good yields.

NHC-Copper(I) Halide-Catalyzed Direct Alkynylation of Trifluoromethyl Ketones on Water

An efficient and easily scalable NHC-copper(I) halide-catalyzed addition of terminal alkynes to 1,1,1-trifluoromethyl ketones, carried out on water for the first time, is reported. A series of addition reactions were performed with as little as 0.1-2.0?mo

Condensed-phase, halogen-bonded CF3I and C2F5I adducts for perfluoroalkylation reactions

A family of practical, liquid trifluoromethylation and pentafluoroethylation reagents is described. We show how halogen bonding can be used to obtain easily handled liquid reagents from gaseous CF3I and CF3CF2I. The synthetic utility of the new reagents is exemplified by a novel direct arene trifluoromethylation reaction as well as adaptations of other perfluoroalkylation reactions. Its (no longer) a gas! A family of practical, liquid trifluoromethylation and pentafluoroethylation reagents enabled by halogen bonding is described. The synthetic utility of these reagents is exemplified by a novel direct arene trifluoromethylation reaction as well as adaptations of other perfluoroalkylation reactions.

FLUOROALKYLATION REAGENTS AND USES THEREOF

Provided herein are halogen-bonded complexes of Formula (I), wherein is a halogen bond; R1 is unsubstituted C1-3 fluoroalkyl; D is N(R2)3, ((R2)2N)2C=NR2, 0=S(R2)2, substituted or unsubstituted heterocyclyl, or substituted or unsubstituted heteroaryl, and wherein R2 and y are as defined herein. D----(I??R1)y (I) Further provided are methods of preparing compounds of Formula (I), compositions, reagents, and kits comprising a compound of Formula (I), and methods for fluoroalkylating an organic compound using a compound of Formula (I).

Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources

The trifluoromethylation of carbonyl compounds is accomplished by the stable (trifluoromethyl)zinc reagent generated and then isolated from CF3I and ZnEt2, which can be utilized as a trifluoromethyl anion source (CF3-). The reaction proceeds smoothly with diamine as a ligand and ammonium salt as an initiator, providing the corresponding trifluoromethylated alcohol products. Moreover, the (trifluoromethyl)zinc reagent can also be employed as a difluorocarbene source (:CF2) not only for gem-difluoroolefination of carbonyl compounds with phosphine but also for gem-difluorocyclization of alkenes or alkynes via the thermal decomposition, respectively.

Polyfluoroalkylation of carbonyl compounds by polyfluoroalkyl anions generated from polyfluorocarboxamides

Polyfluoroalkyl anions, generated by reduction of (polyfluoroalkanoyl)piperidines with Et3BHK, were used for the polyfluoroalkylation of carbonyl compounds. Trifluoromethylation of aromatic aldehydes proceeded in good yields, and that of aliphatic aldehydes afforded a moderate yield. In contrast, the yield was low when the reaction involved benzophenone. Pentafluoroethylation and octafluorobutylation of aldehydes were also carried out by using the corresponding (polyfluoroalkanoyl)piperidines, which were prepared from commercially available polyfluorocompounds. The (polyfluoroalkanoyl)piperidines were also prepared through polyfluorination, and were used in the polyfluoroalkylation of aldehydes.