455-18-5 | Trifluoro-p-tolunitrile

CAS:455-18-5 | Trifluoro-p-tolunitrile,Description

4-(Trifluoromethyl)benzonitrile is a chemical compound known for its unique properties and applications in various fields, including its use as an electrolyte additive in high voltage lithium-ion batteries. Its significance lies in its molecular structure, characterized by the presence of a trifluoromethyl group attached to the benzonitrile moiety, which contributes to its distinctive chemical and physical properties (Huang et al., 2014).

Synthesis Analysis

The synthesis of 4-(Trifluoromethyl)benzonitrile involves several chemical reactions, starting from m-fluoro-(trifluoromethyl)benzene. The process includes bromination, Grignard reaction, cyanidation, and amination, resulting in an overall yield of 49.2%. This synthesis route is highlighted for its environmental friendliness and practicality (Zhang, 2012).

Molecular Structure Analysis

The molecular structure of 4-(Trifluoromethyl)benzonitrile at 123K reveals molecules linked through one C-H...F bond and two C-H...N hydrogen bonds, forming a dense two-dimensional network. The aromatic ring is slightly deformed due to the electronegative groups, indicating the influence of trifluoromethyl and nitrile groups on the overall structure (Boitsov et al., 2002).

Chemical Reactions and Properties

4-(Trifluoromethyl)benzonitrile demonstrates lower oxidative stability compared to common solvents like ethylene carbonate and dimethyl carbonate. It is preferentially oxidized, forming a protective film on lithium nickel manganese oxide cathodes, which prevents electrolyte oxidation decomposition and suppresses manganese dissolution. This property makes it a valuable additive for enhancing the cyclic stability of high voltage lithium-ion batteries (Huang et al., 2014).

Physical Properties Analysis

The study of 4-(Trifluoromethyl)benzonitrile's physical properties is crucial for its application in various fields. However, specific details on its melting point, boiling point, and solubility in different solvents were not directly found in the provided research articles. These properties typically depend on the molecular structure and can influence the compound's applicability in industrial and research settings.

Chemical Properties Analysis

The chemical properties of 4-(Trifluoromethyl)benzonitrile, such as reactivity with nitrogen trifluoride, demonstrate its potential for difluoroamination reactions. The compound's reaction with NF3 at high temperatures indicates its utility in synthesizing various fluorinated organic compounds, showcasing its versatility in organic synthesis (Belter, 2011).

Scientific Research Applications

Application in High Voltage Lithium-Ion Batteries

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• Methods of Application or Experimental Procedures

  The method involves the addition of 0.5 wt.% 4-TB to the electrolyte of the battery. The battery is then subjected to charge-discharge tests to evaluate its performance.

• Results or Outcomes

  The cyclic stability of the LiNi 0.5 Mn 1.5 O 4 cathode is significantly improved by using 0.5 wt.% 4-TB. This indicates that 4-TB can enhance the lifespan and reliability of high voltage lithium-ion batteries.

Synthesis of Fluvoxamine

• Summary of the Application: 4-(Trifluoromethyl)benzonitrile is a key intermediate in the synthesis of fluvoxamine.
• Results or Outcomes: The outcome of this application is the production of fluvoxamine, a medication used for the treatment of obsessive-compulsive disorder.

Nickel-Catalyzed Arylcyanation Reaction

• Summary of the Application: 4-(Trifluoromethyl)benzonitrile participates in nickel-catalyzed arylcyanation reaction of 4-octyne.
• Results or Outcomes: The outcome of this application is the production of a new compound through the arylcyanation reaction.

Safety And Hazards

4-(Trifluoromethyl)benzonitrile causes skin irritation and serious eye irritation. It may cause respiratory irritation and is harmful if swallowed, in contact with skin, or if inhaled. It should be stored in a well-ventilated place and kept container tightly closed.

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