928136-78-1 | 4-Bromo-3-(trifluoromethoxy)benzonitrile

CAS:928136-78-1 | 4-Bromo-3-(trifluoromethoxy)benzonitrile,Description

4-Bromo-3-(trifluoromethoxy)benzonitrile is a chemical compound with the molecular formula C8H3BrF3NO. It is used in various chemical reactions and has a molecular weight of 266.015 Da.

Synthesis Analysis

The synthesis of similar compounds involves processes such as diazotization, formaldoximation, hydrolysis, and cyanation. Another method involves a Stille coupling reaction followed by the conversion of nitrile to amidine using lithium bis (trimethylsilyl)amide.

Molecular Structure Analysis

The molecular structure of 4-Bromo-3-(trifluoromethoxy)benzonitrile includes a bromine atom, a trifluoromethoxy group, and a nitrile group attached to a benzene ring. The compound has a density of 1.8±0.1 g/cm3 and a molar refractivity of 45.8±0.4 cm3.

Chemical Reactions Analysis

While specific chemical reactions involving 4-Bromo-3-(trifluoromethoxy)benzonitrile are not detailed in the search results, similar compounds participate in reactions such as nickel-catalyzed arylcyanation.

Physical And Chemical Properties Analysis

4-Bromo-3-(trifluoromethoxy)benzonitrile has a boiling point of 224.5±40.0 °C at 760 mmHg and a flash point of 89.6±27.3 °C. It has a polar surface area of 33 Å2 and a molar volume of 151.7±5.0 cm3.

Scientific Research Applications

Aryne Route to Naphthalenes

4-Bromo-3-(trifluoromethoxy)benzonitrile is used in generating aryne intermediates for the synthesis of naphthalenes. This process involves the treatment of 4-Bromo-3-(trifluoromethoxy)benzonitrile with lithium diisopropylamide, leading to various phenyllithium intermediates. These intermediates can be converted into 1- and 2-(trifluoromethoxy)naphthalenes, offering new pathways in organic synthesis (Schlosser & Castagnetti, 2001).

Electrolyte Additive in Lithium Ion Batteries

The compound is used as a novel electrolyte additive for high voltage lithium ion batteries, particularly for the LiNi 0.5 Mn 1.5 O 4 cathode. It improves the cyclic stability and capacity retention of the battery significantly (Huang et al., 2014).

Vibrational Spectra Studies

4-Bromo benzonitrile, a related compound, has been studied using density functional theory for vibrational spectra analysis. The research provides insights into the fundamental vibrational frequencies and intensity of vibrational bands, which is essential for understanding the physical properties of such compounds (Krishnakumar, Surumbarkuzhali, & Muthunatesan, 2009).

Steric Pressure in Organic Synthesis

The trifluoromethoxy group in compounds like 4-Bromo-3-(trifluoromethoxy)benzonitrile acts as both an emitter and transmitter of steric pressure in organic synthesis. This property is crucial in understanding and predicting the outcomes of various chemical reactions (Schlosser et al., 2006).

Safety And Hazards

This compound is considered hazardous and should be handled with care. It is toxic if swallowed, in contact with skin, or if inhaled. It is also incompatible with strong oxidizing agents, strong acids, strong bases, and strong reducing agents.

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