718-64-9

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 998, 1965 DOI: 10.1021/jo01015a009

Biochem/physiol Actions

1,1,1,3,3,3-Hexafluoro-2-phenyl-2-propanol is an effective solvent for Cu(0)-mediated single electron transfer-living radical polymerization of methyl methacrylate and polymerization of styrene.

InChI:InChI=1/C9H6F6O/c10-8(11,12)7(16,9(13,14)15)6-4-2-1-3-5-6/h1-5,16H

Upstream product

• 684-16-2 Hexafluoroacetone 
• 71-43-2 benzene 
• 75-91-2 tert.-butylhydroperoxide 
• 32133-82-7 Martins sulfurane 
• 4198-93-0 trityl hydroperoxide 
• 334-99-6 trifluoronitrosomethane 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 88070-48-8 N-methylbenzamide 
• 40999-26-6 Benzoesaeure-i-(1,1,1,3,3,3-hexafluoro-2-phenyl)-propylester 
• 2314-97-8 iodotrifluoromethane 
• 98-88-4 benzoyl chloride 
• 10364-94-0 1-benzoylimidazole 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1548-84-1 pentafluorophenyl benzoate 

Downstream Products

• 19779-35-2 o-(2H-Hexafluor-isopropyl)-phenylisocyanat 
• 70091-67-7 lithium 1,1,1,3,3,3-hexafluoro-2-(2-lithiophenyl)-2-propoxide 
• 91454-72-7 1,1-diphenyl-3,3-bis(trifluoromethyl)-3H-<2,1>benzoxasilole 
• 79209-09-9 1-Methyl-1-phenyl-3,3-bis-trifluoromethyl-1,3-dihydro-benzo[c][1,2]oxasilole 
• 162843-81-4 Benzoic acid 8-(2,2,2-trifluoro-1-phenyl-1-trifluoromethyl-ethoxy)-octyl ester 
• 2402-65-5 1-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-3-nitrobenzene 
• 2402-71-3 3-(2-hydroxy-1,1,1,3,3,3-hexafluoroisopropyl)-bromobenzene 
• 40154-97-0 C₃₂H₂₄F₁₂O₄S 
• 40323-02-2 C₃₈H₃₆F₁₂O₂S 
• 37559-54-9 [2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]benzene 

Relevant academic research and scientific papers

Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF3+, CF3?, and CF3-Reactivity

Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF3+OTf-) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from thianthrene and triflic anhydride. We demonstrate the use of TT-CF3+OTf- in electrophilic, radical, and nucleophilic trifluoromethylation reactions.

COMPLEXES FOR NUCLEOPHILIC, RADICAL, AND ELECTROPHILIC POLYFLUOROALKYLATION

Disclosed herein are borazine complexes and use of the same in perfluoroalkylation reactions.

Design, synthesis and evaluation of novel 19F magnetic resonance sensitive protein tyrosine phosphatase inhibitors

Fluorine is a highly attractive element for both medicinal chemistry and imaging technologies. To facilitate protein tyrosine phosphatase (PTP)-targeted drug discovery and imaging-guided PTP research on fluorine, several highly potent and 19F MR sensitive PTP inhibitors were discovered through a structure-based focused library strategy.

Organocatalysis approach to trifluoromethylation with fluoroform

The organic base methodology exploits an access to generate the "trifluoromethyl anion" for carbonyl, ester, acid halide, epoxide, deuterium donor, and carbon dioxide substrates to afford the trifluoromethylation products with good overall efficiency even in organocatalysis conditions. The NMR analysis of the mixture of fluoroform and P4-base shows no change thereof. However, on addition of electrophiles, the trifluoromethylation products were obtained efficiently.

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.

Structure-Activity Relationships of Organofluorine Inhibitors of β-Amyloid Self-Assembly

A broad group of structurally diverse small organofluorine compounds were synthesized and evaluated as inhibitors of β-amyloid (Aβ) self-assembly. The main goal was to generate a diverse library of compounds with the same functional group and to observe general structural features that characterize inhibitors of Aβ oligomer and fibril formation, ultimately identifying structures for further focused inhibitor design. The common structural motifs in these compounds are CF3-C-OH and CF3-C-NH groups that were proposed to be binding units in our previous studies. A broad range of potential small-molecule inhibitors were synthesized by combining various carbocyclic and heteroaromatic rings with an array of substituents, generating a total of 106 molecules. The compounds were tested by standard methods such as thioflavin-T fluorescence spectroscopy for monitoring fibril formation, biotinyl Aβ1-42 single-site streptavidin-based assays for observing oligomer formation, and atomic force microscopy for morphological studies. These assays revealed a number of structures that show significant inhibition against either Aβ fibril or oligomer formation. A detailed analysis of the structure-activity relationship of anti-fibril and -oligomer properties is provided. These data present further experimental evidence for the distinct nature of fibril versus oligomer formation and indicate that the interaction of the Aβ peptide with chiral small molecules is not stereospecific in nature.

Efficient synthesis of tetradecafluoro-4-phenylheptan-4-ol by a Cannizzaro-type reaction and application of the alcohol as a bulky Martin ligand variant for a new anti-apicophilic phosphorane

Alcohols 8 bearing two identical perfluoroalkyl groups were prepared by the reaction of the corresponding perfluoroalkyl phenyl ketones 7 with 0.5 equivalents of t-BuOK via Cannizzaro-type disproportionation. Utilizing the new bulky bidentate ligand with two n-C3F7 groups generated from 8c, anti-apicophilic phosphorane 5a and its stable isomer 6a were synthesized. The crystal structures of 5a and 6a were slightly affected by the steric repulsion of heptafluoropropyl groups. Kinetic studies on the isomerization of 5a to 6a showed that the new ligand was effective for decreasing the isomerization rate compared with its C2F5 analog 3a to about half.

Convenient syntheses of 1,1,1,3,3,3-hexafluoro-2-organyl-propan-2-ols and the corresponding trimethylsilyl ethers

A new convenient synthetic procedure to obtain various 1,1,1,3,3,3- hexafluoro-2-organyl-propan-2-ols and the corresponding trimethylsilyl ethers has been worked out starting from anhydrides or activated esters of carboxylic acids and trimethyl(trifluoromethyl)silane in the presence of tetramethylammonium fluoride. Conditions for the selective formation of 1,1,1,3,3,3-hexafluoro-2-organyl-propan-2-ols as well as the trimethylsilyl derivatives have been found.

Trifluoromethylation of carbonyl compounds with sodium trifluoroacetate

In the presence of copper(I) iodide as catalyst, a variety of carbonyl compounds, such as aldehydes, ketones and acid anhydrous, could be trifluoromethylated with sodium trifluoroacetate to give the corresponding alcohols in moderate to high yields, and a possible mechanism was proposed to explain the roles of catalyst and solvent in the reaction system.

Sodium trifluoroacetate: An efficient precursor for the trifluoromethylation of aldehydes

In a convenient and efficient procedure, the nucleophilic trifluoromethylation of aldehydes with sodium trifluoroacetate was achieved, using copper(I) halides as the catalyst.