731002-50-9 | 3-hydroxy-4-(trifluoromethyl)benzonitrile

CAS:731002-50-9 | 3-hydroxy-4-(trifluoromethyl)benzonitrile,Description

3-Hydroxy-4-(trifluoromethyl)benzonitrile is a compound that has not been directly studied in the provided papers. However, its structural analogs and related compounds have been the subject of various research efforts. These studies have explored the properties, synthesis, and applications of benzonitrile derivatives, particularly those with trifluoromethyl groups, which can significantly influence the chemical behavior and physical properties of these molecules.

Synthesis Analysis

The synthesis of benzonitrile derivatives often involves regioselective cycloaddition reactions, as seen in the case of trifluoromethanesulfonyloxy-group-directed synthesis of functionalized benzo-fused heterocycles. Additionally, the synthesis of complex molecules like 3-(2,6-bis(trifluoromethyl)phenoxy)-6-(prop-2-yn-1-yloxy)phthalonitrile has been achieved, showcasing the versatility of trifluoromethyl-substituted benzonitriles in forming novel compounds through reactions such as click chemistry.

Molecular Structure Analysis

The molecular structure of 4-(trifluoromethyl)benzonitrile has been characterized by X-ray crystallography, revealing a dense two-dimensional network formed through hydrogen bonding without significant pi-pi ring interactions. The presence of electronegative groups like trifluoromethyl can cause slight deformations in the aromatic ring.

Chemical Reactions Analysis

Trifluoromethyl groups in benzonitrile derivatives influence the reactivity in various chemical reactions. For instance, the presence of a trifluoromethyl group in 1-trifluoromethyl-4-vinyl-benzene reduces the activation energy in [3+2] cycloaddition reactions, which can enhance the experimental yield. Similarly, the triflyloxy group in benzynes affects the regiocontrol of cycloaddition reactions, demonstrating the impact of trifluoromethyl substituents on the chemical reactivity of benzonitrile derivatives.

Physical and Chemical Properties Analysis

The physical properties of benzonitrile derivatives, such as smectic liquid-crystalline behavior, are influenced by the presence of perfluoroalkyl groups. These molecules exhibit smectic A and B phases, with layer spacings that are multiples of the calculated molecular length, indicating the role of fluorophilic and polar interactions in their molecular arrangements. In the context of electrochemistry, 4-(trifluoromethyl)benzonitrile has been used as an electrolyte additive in lithium-ion batteries, improving cyclic stability and forming a protective film on the cathode, which is attributed to its lower oxidative stability compared to other components in the electrolyte.

Scientific Research Applications

1. Dermatological Applications

3-Hydroxy-4-(trifluoromethyl)benzonitrile and related compounds have been investigated for their potential in dermatological applications. For instance, 4-((1R,2R)-2-hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile [PF-0998425, (-)- 6a] is explored as a nonsteroidal androgen receptor antagonist. It shows promise for sebum control and treating androgenetic alopecia, with the potential to minimize unwanted systemic side effects due to rapid systemic metabolism and reduced phototoxicity risks (Li et al., 2008).

2. Pharmaceutical Synthesis

(S)-3-(5-Oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinolin-4-yl)benzonitrile, a related compound, is developed as a potassium-channel opener for treating urinary urge incontinence. Its synthesis involves an unsymmetrical Hantzsch reaction, critical for optimizing yield and impurity control, and has been successfully scaled up for plant-scale production (Hopes, Parker, & Patel, 2006).

3. Energy Storage Applications

In energy storage, 4-(Trifluoromethyl)-benzonitrile (4-TB) is used as an electrolyte additive for high voltage lithium-ion batteries. This compound significantly improves the cyclic stability of LiNi 0.5 Mn 1.5 O 4 cathodes, leading to enhanced capacity retention and suppressing manganese dissolution from the cathode material (Huang et al., 2014).

4. Solar Energy Applications

A perfluorinated compound, 4-amino-2-(trifluoromethyl)benzonitrile (ATMB), is utilized as an additive in polymer solar cells. It enhances power conversion efficiency by improving short circuit current and fill factor, facilitated by the ordering of P3HT chains and increased crystal size (Jeong, Woo, Lyu, & Han, 2011).

Safety And Hazards

The compound is considered hazardous. It has a GHS07 pictogram and the signal word is "Warning". The hazard statements include H302, and the precautionary statements include P280-P305+P351+P338.

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