402-50-6 | 4-(TRIFLUOROMETHYL)STYRENE

CAS:402-50-6 | 4-(TRIFLUOROMETHYL)STYRENE,Description

Synthesis Analysis

The synthesis of α-(Trifluoromethyl)styrenes can be achieved through coupling reactions of 2-bromo-3,3,3-trifluoropropene with aryl iodides, utilizing (3,3,3-trifluoroprop-1-en-2-yl)boronic acid as an intermediate. These styrenes are precursors to 4-trifluoromethyl- or 4-difluoromethylene-substituted isochromanes and isothiochromanes through intramolecular nucleophilic addition or substitution under basic conditions (Ichikawa, Ikeda, & Hattori, 2009).

Molecular Structure Analysis

The molecular structure of 4-(Trifluoromethyl)styrene is characterized by the presence of the trifluoromethyl group which is a strong electron-withdrawing group. This group affects the electronic distribution on the benzene ring and influences the reactivity of the compound. The presence of this group also impacts the molecular geometry and steric interactions within the molecule and its reactions.

Chemical Reactions and Properties

4-(Trifluoromethyl)styrene undergoes various chemical reactions, including photoredox catalysis activated by visible light, leading to the difunctionalization of styrenes with trifluoromethyl groups and hydroxyl groups originating from molecular oxygen. This process showcases the compound's ability to participate in radical reactions under mild conditions (Li et al., 2015).

Physical Properties Analysis

The physical properties of 4-(Trifluoromethyl)styrene, such as boiling point, melting point, and solubility, are significantly influenced by the trifluoromethyl group. This group increases the compound's hydrophobicity and lowers its polarity compared to styrene without any fluorinated substituents. These properties are critical when considering the compound's applications in material science and polymer chemistry.

Chemical Properties Analysis

The chemical properties of 4-(Trifluoromethyl)styrene, including its reactivity towards electrophiles, nucleophiles, and radicals, are markedly affected by the electron-withdrawing nature of the trifluoromethyl group. This group stabilizes carbocationic intermediates and can influence the direction and outcome of addition reactions. It also plays a crucial role in the polymerization processes, affecting the kinetics and the properties of the resulting polymers (Yoshida & Sugita, 1998).

Scientific Research Applications

Organic Synthesis

• Field : Organic Chemistry
• Application : 4-(Trifluoromethyl)styrene derivatives are versatile synthetic intermediates for the preparation of more complex fluorinated compounds. They have been successfully utilized in C–F bond activation in a CF3 group, mainly including anionic S N 2′-type substitution, cationic S N 1′-type substitution, ipso-substitution and defluorinative functionalization with transition metals or photoredox catalysts.
• Methods : The synthesis of α-trifluoromethylstyrenes and their applications in organic synthetic chemistry have been systematically summarized. The methods involve various types of substitutions and functionalizations, often catalyzed by transition metals or photoredox catalysts.
• Results : The use of 4-(Trifluoromethyl)styrene in these reactions has enabled the construction of cycloalkanes and cycloalkenes containing fluoro or trifluoromethyl groups.

Polymerization

• Field : Polymer Chemistry
• Application : 4-(Trifluoromethyl)styrene is used in the controlled radical copolymerization with styrenes to produce partially fluorinated polymers with trifluoromethyl groups in the main chain.
• Methods : The polymerization method applied is the controlled radical polymerization, which is effective for the polymerization of styrene. Nitroxide-mediated polymerization has been shown to be effective. The content ratio of 4-(Trifluoromethyl)styrene in the copolymer can be controlled between 10% and 40% by changing its monomer ratio.
• Results : The thermal stability as well as water and oil repellency of the synthesized polymers with different composition ratios and substituents were evaluated.

Organic Chemical Synthesis Intermediate

• Field : Organic Chemistry
• Application : 4-(Trifluoromethyl)styrene is used as an organic chemical synthesis intermediate. It is a versatile synthetic intermediate for the preparation of more complex fluorinated compounds.
• Methods : The methods involve various types of substitutions and functionalizations, often catalyzed by transition metals or photoredox catalysts.
• Results : The use of 4-(Trifluoromethyl)styrene in these reactions has enabled the construction of cycloalkanes and cycloalkenes containing fluoro or trifluoromethyl groups.

Polymerization Tools

• Field : Polymer Chemistry
• Application : 4-(Trifluoromethyl)styrene is used in the controlled radical copolymerization with styrenes to produce partially fluorinated polymers with trifluoromethyl groups in the main chain.
• Methods : The polymerization method applied is the controlled radical polymerization, which is effective for the polymerization of styrene. Nitroxide-mediated polymerization has been shown to be effective.
• Results : The thermal stability as well as water and oil repellency of the synthesized polymers with different composition ratios and substituents were evaluated.

Synthesis of Fluorinated Compounds

• Field : Organic Chemistry
• Application : 4-(Trifluoromethyl)styrene derivatives are versatile synthetic intermediates for the preparation of more complex fluorinated compounds. They have been successfully utilized in C–F bond activation in a CF3 group, mainly including anionic S N 2′-type substitution, cationic S N 1′-type substitution, ipso-substitution and defluorinative functionalization with transition metals or photoredox catalysts.
• Methods : The synthesis of α-trifluoromethylstyrenes and their applications in organic synthetic chemistry have been systematically summarized. The methods involve various types of substitutions and functionalizations, often catalyzed by transition metals or photoredox catalysts.
• Results : The use of 4-(Trifluoromethyl)styrene in these reactions has enabled the construction of cycloalkanes and cycloalkenes containing fluoro or trifluoromethyl groups.

Synthesis of Partially Fluorinated Polymers

• Field : Polymer Chemistry
• Application : 4-(Trifluoromethyl)styrene is used in the controlled radical copolymerization with styrenes to produce partially fluorinated polymers with trifluoromethyl groups in the main chain.
• Methods : The polymerization method applied is the controlled radical polymerization, which is effective for the polymerization of styrene. Nitroxide-mediated polymerization has been shown to be effective. The content ratio of 4-(Trifluoromethyl)styrene in the copolymer can be controlled between 10% and 40% by changing its monomer ratio.
• Results : The thermal stability as well as water and oil repellency of the synthesized polymers with different composition ratios and substituents were evaluated.

Safety And Hazards

• Precautionary Measures : Handle away from heat, sparks, and open flames. Ground/bond containers and equipment. Use explosion-proof electrical/ventilating/lighting equipment. Wear protective gear. In case of fire, use appropriate extinguishing agents .

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