60686-64-8

Usage

Uses

Used in Scientific Research:
2,2,2-Trifluoro-1-(9-anthryl)ethanol is used as a fluorescent probe for fluorescence studies due to the anthracene group's ability to absorb and emit light, which is crucial for analyzing molecular interactions and processes in various research fields.
Used in Fluorescence Imaging:
In the field of fluorescence imaging, 2,2,2-Trifluoro-1-(9-anthryl)ethanol is employed as a fluorescent label to enhance the visibility of specific molecules or cellular structures, facilitating the study of biological processes and disease mechanisms.
Used in Drug Discovery:
2,2,2-Trifluoro-1-(9-anthryl)ethanol is utilized as a chemical intermediate in the synthesis of potential drug candidates, particularly those targeting complex biological systems. Its unique structural features may contribute to the development of novel therapeutic agents.
Used in Material Science:
In material science, 2,2,2-Trifluoro-1-(9-anthryl)ethanol is used as a component in the development of advanced materials with specific optical properties, such as organic light-emitting diodes (OLEDs) and photovoltaic cells, where its fluorescence characteristics can be harnessed for improved performance.

Upstream product

• 75-63-8 Bromotrifluoromethane 
• 642-31-9 9-anthracene aldehyde 
• 120-12-7 anthracene 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 
• 75-46-7 trifluoromethan 
• 1447665-42-0 (1-(anthracen-9-yl)-2,2,2-trifluoroethoxy)tributylstannane 

Downstream Products

• 104449-58-3 phenylglyoxylate du 2,2,2-trifluoro-1-(9-anthryl)ethanol 
• 53531-31-0 1-(9-anthracenyl)-2,2,2-trifluoroethan-1-one 
• 104449-63-0 Hydroxy-phenyl-acetic acid 1-anthracen-9-yl-2,2,2-trifluoro-ethyl ester 
• 105748-32-1 (2-Hydroxy-1,2-diphenyl-ethyl)-carbamic acid 1-anthracen-9-yl-2,2,2-trifluoro-ethyl ester 
• 1360454-55-2 (R)-1-(anthracen-9-yl)-2,2,2-trifluoroethyl propanoate 
• 60646-30-2 (S)-2,2,2-trifluro-1-(anthryl)ethanol 
• 53531-34-3 (R)-2,2,2-trifluoro-1-(9-anthryl)ethanol 
• 77507-50-7 N-Benzyl-α-<1-(9-anthryl)-2,2,2-trifluoroethoxy>acetamide 
• 114087-00-2 2-Cyclohexyl-but-3-enoic acid 1-anthracen-9-yl-2,2,2-trifluoro-ethyl ester 
• 111015-35-1 2-Hydroxy-2-phenyl-propionic acid 1-anthracen-9-yl-2,2,2-trifluoro-ethyl ester 
• 53531-34-3 (-)-2,2,2-trifluoro-1-(9-anthryl)ethanol 
• 60646-30-2 (+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol 

Relevant academic research and scientific papers

Synthesis and structural study of the enantiomers of α, α′-bis(trifluoromethyl)-10,10′-(9,9′-bianthryl) dimethanol as a chiral solvating agent

We describe the synthesis, the structure, and the behavior as a chiral solvating agent of the enantiomers of α,α′- bis(trifluoromethyl)-10,10′-(9,9′-biantryl)dimethanol. The thermodynamics of several associations are presented. We conclude that the association needs the approximation of the aromatic systems and that the geometry of complexation is the main factor that defines the enantiodiscrimination.

Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N-Sulfinylimines

A micro-flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro-flow transformation of N-sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility of this micro-flow synthesis, the formal micro-flow synthesis of Efavirenz is described.

METHOD FOR PRODUCING TRIFLUOROMETHYL GROUP-CONTAINING ALCOHOLS

PROBLEM TO BE SOLVED: To provide a method for producing trifluoromethyl group-containing alcohols useful as synthetic intermediates for medicines and agrochemicals. SOLUTION: This invention relates to a method for producing trifluoromethyl group-containing alcohols expressed by a formula (2), comprising: making carbonyl compounds expressed by a formula (1) react with trifluoromethane in an organic solvent in the presence of polyvalent ethers and potassium tert-butoxide, or kalium hexamethyldisilazide. (R1 and R2 are each independently a phenyl group etc.; R2 may combine with R1, to form a ring, and both R1 and R2 are not hydrogen atoms). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

A method of manufacturing a trifluoromethyl group-containing compound

PROBLEM TO BE SOLVED: To provide a method for producing a trifluoromethyl group-containing compound useful as a synthetic intermediate for a pharmaceutical or an agricultural chemical product.SOLUTION: There is provided a method for producing a trifluoromethyl group-containing compound represented by the following general formula (2) which is obtained by reacting a carbonyl compound having a specific structure with trifluoromethane and an organic base in an organic solvent (wherein, Rrepresents a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 10 carbon atoms, a phenyl group, a substituted phenyl group, a naphthyl group, a substituted naphthyl group, an ethenyl group, a 2-phenylethenyl group, a 9-anthryl group or a hetero ring; Rrepresents a hydrogen atom, a methyl group or a phenyl group.)

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.

DIRECT TRIFLUOROMETHYLATIONS USING TRIFLUOROMETHANE

A direct trifluoromethylation method preferably using a trifluoromethane as a fluoro-methylating species. In particular, the present method is used for preparing a trifluoromethylated substrate by reacting a fluoromethylatable substrate with a trifiuoromethylating agent in the presence of an alkoxide or metal salt of silazane under conditions sufficient to trifluoromethylate the substrate; wherein the fluoromethylatable substrate includes chlorosilanes, carbonyl compounds such as esters, aryl halides, aldehydes, ketones, chalcones, alkyl formates, alkyl halides, aryl halides, alkyl borates, carbon dioxide or sulfur.

A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform

A simple strategy avoiding the decomposition of a naked trifluoromethyl anion to difluorocarbene by a sterically very demanding organo-superbase without the help of a trifluoromethyl anion reservoir such as DMF is reported. The direct non-metallic trifluoromethylation of carbonyl compounds using fluoroform in the presence of t-Bu-P4 base afforded trifluoromethyl alcohols in high yields.

Trifluoromethylation of ketones and aldehydes with Bu3SnCF 3

The (trifluoromethyl)stannane reagent, Bu3SnCF3, was found to react under CsF activation with ketones and aldehydes to the corresponding trifluoromethylated stannane ether intermediates at room temperature in high yield. Only a mildly acidic extraction (aqueous NH 4Cl) is required to release the corresponding trifluoromethyl alcohol products. The protocol is compatible with acid-sensitive functional groups.

Taming of fluoroform: Direct nucleophilic trifluoromethylation of Si, B, S, and C centers

Fluoroform (CF3H), a large-volume by-product of the manufacture of Teflon, refrigerants, polyvinylidene fluoride (PVDF), fire-extinguishing agents, and foams, is a potent and stable greenhouse gas that has found little practical use despite the growing importance of trifluoromethyl (CF3) functionality in more structurally elaborate pharmaceuticals, agrochemicals, and materials. Direct nucleophilic trifluoromethylation using CF3H has been a challenge. Here, we report on a direct trifluoromethylation protocol using close to stoichiometric amounts of CF3H in common organic solvents such as tetrahydrofuran (THF), diethyl ether, and toluene. The methodology is widely applicable to a variety of silicon, boron, and sulfur-based electrophiles, as well as carbon-based electrophiles.

Reactions of Trifluoromethyl Bromide and Related Halides: Part 9. Comparison between Additions to Carbonyl Compounds, Enamines, and Sulphur Dioxide in the Presence of Zinc

A Barbier procedure, under moderate pressure, was used for the trifluoromethylation of various carbonyl compounds, starting from trifluoromethyl bromide and zinc in pyridine.Trifluoromethyl methanols were obtained from aldehydes and trifluoromethyl ketones from activated esters.Ethyl benzoate, or acetone, induced the formation of the solvated trifluoromethylzinc derivatives which did not react with carbonyl cpompounds.Consequently, the Barbier condensation in that case was considered to involve nascent organometallics reacting near the zinc surface.The reaction with sulphur dioxide, leading to trifluoromethanesulphinate, showed striking differences from that of carbonyl compounds.It was shown that the main pathway occcured in solution.This condensation was interpreted by the initial formation of sulphur dioxide radical anion, which reacts with trifluoromethyl bromide by a single-electron-transfer process.Attempts to condense iminium salts failed when a hydrogen atom was lacking in the α position.When the iminium ion can be transformed in situ to an enamine, a reaction occured, leading to α-trifluoromethyl ketones.This condensation was interpreted by a chain mechanism involving trifluoromethyl radicals.