402-50-6

Basic information

• Product Name: 4-(TRIFLUOROMETHYL)STYRENE
• Synonyms: 4-VINYLBENZOTRIFLUORIDE;4-(TRIFLUOROMETHYL)STYRENE;4-(Trifluoromethyl)styrene,4-Vinylbenzotrifluoride;4-(Trifluoromethyl)styrene, stabilized with 0.1% 4-tert-butylcatechol, 98+%;4-(Trifluoromethyl)styrene 98%;4-(TrifluoroMethyl)styrene, 98%, stab.;4-Vinylbenzotrifluoride, 1-Ethenyl-4-(trifluoromethyl)benzene;1-ethenyl-4-(trifluoroMethyl)benzene
• CAS NO: 402-50-6
• Molecular Formula: C₉H₇F₃
• Molecular Weight: 172.15
• Mol File: 402-50-6.mol
• Article Data: 81

Chemical Properties

• Boiling Point: 65-66 °C40 mm Hg(lit.)
• Flash Point: 108 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.165 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.466(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 1863548
• CAS DataBase Reference: 4-(TRIFLUOROMETHYL)STYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TRIFLUOROMETHYL)STYRENE(402-50-6)
• EPA Substance Registry System: 4-(TRIFLUOROMETHYL)STYRENE(402-50-6)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36/37
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 402-50-6(Hazardous Substances Data)

Usage

Description

4-(Trifluoromethyl)styrene, also known as α,α,α-trifluoro-4-vinyltoluene, is an organic compound that belongs to the family of styrene derivatives. It is characterized by the presence of a trifluoromethyl group attached to the 4-position of the styrene molecule. 4-(TRIFLUOROMETHYL)STYRENE exhibits a clear light yellow liquid appearance and is known for its unique chemical properties, making it a versatile building block in the synthesis of various organic compounds.

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

• 1737-26-4 1-(4-trifluorophenyl)ethanol 
• 77207-67-1 <2-ethyl>trimethylammonium iodide 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 108-05-4 vinyl acetate 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 4627-10-5 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane 
• 455-13-0 4-Iodobenzotrifluoride 
• 78599-06-1 dimethyl(thiophen-2-yl)(vinyl)silane 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 98-56-6 4-chlorobenzotrifluoride 
• 146397-87-7 p-(trifluoromethyl)phenyl trifluoromethanesulfonate 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 75-07-0 acetaldehyde 

Downstream Products

• 42006-43-9 (E)-1-(prop-1-en-1-yl)-4-(trifluoromethyl)benzene 
• 134904-86-2 2-Methyl-2-(4-trifluoromethylphenyl)acetic acid 
• 1200806-87-6 N-(((1S,2R)-(-)-1-phenyl-2-(4-(trifluoromethyl)phenyl)cyclopropyl)methyl)propane-2-sulfonamide 
• 1200806-73-0 (1S,2R)-(+)-1-phenyl-2-(4-(trifluoromethyl)phenyl)cyclopropanecarbaldehyde 
• 175605-64-8 1-(4-(trifluoromethyl)phenyl)ethane-1,2-diol 
• 1977-60-2 ethyl 2-(4-(trifluoromethyl)phenyl)cyclopropanecarboxylate 
• 929256-65-5 (E)-2-(4-Trifluoromethyl-phenyl)-ethenesulfonyl chloride 
• 252877-04-6 (2R)-2-[4-(trifluoromethyl)phenyl]oxirane 

Relevant articles and documents

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.

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.

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.