384-64-5

Usage

Uses

Used in Pharmaceutical Industry:
3-(TRIFLUOROMETHYL)STYRENE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with enhanced properties.
Used in Agrochemical Industry:
3-(TRIFLUOROMETHYL)STYRENE is used as a precursor in the production of agrochemicals, aiding in the creation of more effective and targeted pesticides and other agricultural chemicals.
Used in Polymer Industry:
3-(TRIFLUOROMETHYL)STYRENE is used as a monomer in the production of specialty polymers, which are valued for their improved thermal and chemical resistance, making them suitable for various high-performance applications.
Used in Organic Synthesis:
3-(TRIFLUOROMETHYL)STYRENE is used as a valuable reagent in organic synthesis, particularly for the preparation of aryltrifluoromethyl compounds, which have significant applications in medicinal chemistry and material science.
It is crucial to handle 3-(TRIFLUOROMETHYL)STYRENE with care due to its flammable nature and potential health hazards if not managed properly.

InChI:InChI=1/C9H7F3/c1-7(9(10,11)12)8-5-3-2-4-6-8/h2-6H,1H2

Upstream product

• 64-18-6 formic acid 
• 73572-26-6 1-phenyl-1-methyl-2,2,2-trifluoroethyl tosylate 
• 591-50-4 iodobenzene 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 1516-08-1 ethanol-d6 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 1186-52-3 tetradeuterioacetic acid 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 38701-74-5 2-deuterio-2-deuteriooxy-1,1,1,3,3,3-hexafluoropropane 
• 64-19-7 acetic acid 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 124-63-0 methanesulfonyl chloride 
• 384-67-8 2-chloro-2,2-difluoroacetophenone 

Downstream Products

• 138536-05-7 2-Methyl-3,5-diphenyl-5-trifluoromethyl-isoxazolidine 
• 140428-08-6 4-trifluoromethyl-4-phenyl-2-cyclohexen-1-one 
• 116076-84-7 4-phenyl-5,5,5-trifluoro-pentanenitrile 
• 159383-84-3 (-)-(2R)-3,3,3-trifluoro-2-phenylpropane-1,2-diol 
• 52356-12-4 (S)-1,1,1-trifluoro-2-phenyl-2,3-propanediol 
• 426-54-0 1,1,1-trifluoro-2-phenylpropan-2-ol 
• 938-78-3 (1,1-difluorobut-1-en-2-yl)benzene 
• 89264-12-0 1,1-difluoro-2-phenyl-1,4-pentadiene 

Relevant academic research and scientific papers

Site-Selective Defluorinative sp3C-H Alkylation of Secondary Amides

A site-selective defluorinative sp3 C-H alkylation of secondary amides that rapidly and reliably incorporates gem-difluoroalkene motifs into previously unfunctionalized sp3 sites is disclosed. This protocol is distinguished by its mild conditions, wide scope, and exquisite site-selectivity, thus unlocking a new platform to introduce carbonyl isosteres at saturated hydrocarbon sites.

Photoredox/Hydrogen Atom Transfer Cocatalyzed C-H Difluoroallylation of Amides, Ethers, and Alkyl Aldehydes

Herein, we report a method that combines hydrogen atom transfer and photoredox catalysis to achieve the dehydrogenative difluoroallylation of amides, ethers, and alkyl aldehydes. This operationally convenient method transforms a broad scope of substrates into the corresponding gem-difluoroalkenes via the construction of C(sp3)-C(sp3) or C(sp3)-C(sp2) bonds. Excellent functional group compatibility and high selectivity make this method have a wide range of substrate types and render it suitable for late-stage modification of pharmaceutical intermediates.

Photoredox relay-catalyzedgem-difluoroallylation of alkyl iodides

Herein, a new example of relay catalysis, using a combination of Mn2(CO)10and an iridium-based photocatalyst, is reported. In our relay catalytic reaction, the Mn catalyst and iridium-based photocatalyst catalyze the reaction at different stages in the desired sequence under the same reaction conditions, and do not inhibit each other. This convenient method transforms a broad scope of alkyl iodides into the correspondinggem-difluoroalkenesviaC(sp3)-C(sp3) bond construction. The protocol has good functional group tolerance and is suitable for the late-stage modification of multifunctional complex molecules.

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol

Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.

Electrochemical heterodifunctionalization of α-CF3alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols

An unprecedented electrochemical heterodifunctionalization of α-CF3alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond in a single operation. Consequently, a series of potentially medicinally valuable and densely functionalized α-trifluoromethyl-β-sulfonyl tertiary alcohols were assembled under mild conditions. Electrochemically-driven oxidative 1,2-difunctionlization of electron-deficient alkenes well obviates the need for oxidizing reagents, thus rendering this protocol more eco-friendly.

Glycosyl-Radical-Based Synthesis of C-Alkyl Glycosides via Photomediated Defluorinative gem-Difluoroallylation

We have developed a stereoselective, glycosyl radical-based method for the synthesis of C-alkyl glycosides via a photomediated defluorinative gem-difluoroallylation reaction. We demonstrate for the first time that glycosyl radicals, generated from glycosyl bromides, can readily participate in a photomediated radical polar crossover process, affording a diverse array of gem-difluoroalkene containing C-glycosides. Notable features of this method include scalability, mild conditions, broad substrate scope, and suitability for the late-stage modification of complex molecules.

Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHF2-Containing Trisubstituted Cyclopropanes

The difluoromethyl (CHF2) group has attracted significant attention in drug discovery and development efforts, owing to its ability to serve as fluorinated bioisostere of methyl, hydroxyl, and thiol groups. Herein, we report an efficient biocat

One-pot synthesis of α-trifluoromethylstyrenes from aryl ketones and the Ruppert–Prakash reagent

A new synthesis of α-trifluoromethylstyrenes from aromatic ketones and (trifluoromethyl) trimethylsilane is described. The reaction involves nucleophilic trifluoromethylation and elimination of trimethylsilanol, which are performed within one reaction fla

Visible-Light-Induced Deoxygenation/Defluorination Protocol for Synthesis of γ,γ-Difluoroallylic Ketones

Herein, we describe an efficient, practical photocatalytic deoxygenation/defluorination protocol for the synthesis of γ,γ-difluoroallylic ketones from commercially available aromatic carboxylic acids, triphenylphosphine, and α-trifluoromethyl alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this method, we accomplished the late-stage functionalization of several bioactive molecules.

Photoinduced Single-Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC–Borane

A photoinduced SET process enables the direct B?H bond activation of NHC–boranes. In contrast to common hydrogen atom transfer (HAT) strategies, this photoinduced reaction simply takes advantage of the beneficial redox potentials of NHC–boranes, thus obviating the need for extra radical initiators. The resulting NHC–boryl radical was used for the borylation of a wide range of α-trifluoromethylalkenes and alkenes with diverse electronic and structural features, providing facile access to highly functionalized borylated molecules. Labeling and photoquenching experiments provide insight into the mechanism of this photoinduced SET pathway.