402-50-6

Usage

Uses

Used in Chemical Synthesis:
4-(Trifluoromethyl)styrene is used as an organic chemical synthesis intermediate for the production of a wide range of compounds. Its unique structure, which includes the electron-withdrawing trifluoromethyl group and the vinyl group, allows it to participate in various chemical reactions, such as electrophilic substitution, free radical reactions, and cross-coupling reactions. This versatility makes it a valuable starting material for the synthesis of pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(trifluoromethyl)styrene is used as a key intermediate in the synthesis of various drug molecules. The trifluoromethyl group is known to enhance the lipophilicity, metabolic stability, and overall bioactivity of the resulting compounds. As a result, 4-(trifluoromethyl)styrene plays a crucial role in the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
4-(Trifluoromethyl)styrene is also utilized in the agrochemical industry for the synthesis of novel pesticides and insecticides. The introduction of the trifluoromethyl group into the molecular structure can lead to enhanced biological activity and selectivity, making it an attractive option for the development of more effective and environmentally friendly agrochemicals.
Used in Advanced Materials:
In the field of advanced materials, 4-(trifluoromethyl)styrene is employed as a building block for the synthesis of various polymers and materials with unique properties. The incorporation of the trifluoromethyl group can significantly alter the physical and chemical properties of the resulting materials, such as their thermal stability, mechanical strength, and optical properties. This makes 4-(trifluoromethyl)styrene a valuable component in the development of innovative materials for applications in electronics, optics, and other high-tech industries.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1795, 1988 DOI: 10.1080/00397918808060934

Upstream product

• 26536-36-7 2-(p-Trifluoromethylphenyl)-aethyltrimethylammoniumbromid 
• 1737-26-4 1-(4-trifluorophenyl)ethanol 
• 138351-85-6 1-(4-trifluoromethylphenyl)-2-trimethylsilylethanol 
• 77207-67-1 <2-ethyl>trimethylammonium iodide 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 19493-09-5 Methylenetriphenylphosphorane 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 75-07-0 acetaldehyde 
• 455-13-0 4-Iodobenzotrifluoride 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 146397-87-7 p-(trifluoromethyl)phenyl trifluoromethanesulfonate 
• 98-56-6 4-chlorobenzotrifluoride 
• 593-60-2 Vinyl bromide 

Downstream Products

• 74672-14-3 2-Methyl-4-(p-trifluormethyl)-1-penten 
• 74672-15-4 2-Methyl-5-(p-trifluormethylphenyl)-1-penten 
• 89619-12-5 1-(1,2-dibromoethyl)-4-(trifluoromethyl)benzene 
• 1059140-27-0 1-(2-bromovinyl)-4-(trifluoromethyl)benzene 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 27190-69-8 1-ethyl-4-(trifluoromethyl)benzene 
• 93628-97-8 1-(2-nitrovinyl)-4-trifluoromethylbenzene 

Relevant academic research and scientific papers

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent

A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.

Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids

A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.

KO-t-Bu Catalyzed Thiolation of β-(Hetero)arylethyl Ethers via MeOH Elimination/hydrothiolation

Herein, we describe a KO-t-Bu catalyzed thiolation of β-(hetero)arylethyl ethers through MeOH elimination to form (hetero)arylalkenes followed by anti-Markovnikov hydrothiolation to afford linear thioethers. The system works well with a variety of β-(hetero)arylethyl ethers, including electron-deficient, electron-neutral, electron-rich, and branched substrates and a range of aliphatic and aromatic thiols.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylationviaradical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.

Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes

Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized. Excellent conversion (up to 99%) and selectivity can be achieved in the hydrogenation of terminal alkynes catalyzed by P-BPh3. This catalytic system works quite well for different substrates. In addition, the P-BPh3 can be easily recycled.

Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid

Rapid derivatization of chiral 1,2-diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton-coupled circular dichroic (ECCD) of the naphthyl groups. Aryl- and alkyl-substituted 1,2-diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.

Synthesis method of monosubstituted styrene

The invention discloses a synthetic method of monosubstituted styrene. According to the method, monosubstituted benzaldehyde and methyltriphenylphosphonium bromide are used as initial raw materials, tetrahydrofuran is used as a solvent, strong base without nitrogen protection and low-temperature reaction conditions is used for reaction at normal temperature and normal pressure, and after the reaction is finished, a flash column chromatography method is used for post-treatment to obtain monosubstituted styrene. According to the method, water-free and oxygen-free harsh operation conditions are avoided, and the synthesis cost is reduced; the post-treatment process is simplified, quenching and extraction operations are not needed, the post-treatment time is shortened, a large amount of eluentdoes not need to be used, and the product loss is reduced.

Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing C-Vinyl Glycosides

A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.