2,2'-Bis(trifluoromethyl)benzidine: properties, applications and safety

General Description

2,2'-Bis(trifluoromethyl)benzidine (BTB) is an organic compound with various notable properties. It is a solid crystalline substance with a white to off-white powder or crystal appearance. BTB has a high melting point and is sparingly soluble in water but readily dissolves in organic solvents. It exhibits good stability under normal conditions and can undergo different chemical reactions. The presence of trifluoromethyl groups in BTB influences its unique reactivity. It is utilized in the synthesis of high-performance resins, where it contributes to improved mechanical and dielectric properties. BTB also finds application in the adsorption of pollutants, particularly aflatoxins. However, it is important to note that BTB is highly toxic and potentially carcinogenic, requiring strict safety measures when handling.

Figure 1. 2,2'-Bis(trifluoromethyl)benzidine

Properties

2,2'-Bis(trifluoromethyl)benzidine is an organic compound with notable properties. It has a molecular formula of C14H10F6N2 and a molecular weight of approximately 342.24 g/mol. BTB appears as a solid crystalline substance in the form of white to off-white powder or crystals. It has a relatively high melting point of around 180-185°C. In terms of solubility, BTB is sparingly soluble in water but readily dissolves in various organic solvents such as ethanol, methanol, chloroform, and dichloromethane. BTB exhibits good stability under normal conditions, showing resistance to light, heat, and moisture. Due to its versatility as an organic compound, it can undergo different types of chemical reactions, including oxidation, reduction, and substitution reactions. The presence of trifluoromethyl groups in BTB contributes to its unique reactivity, influencing its chemical behavior. These properties make 2,2'-Bis(trifluoromethyl)benzidine valuable in various industries, serving as an intermediate or building block for the synthesis of pharmaceuticals, agrochemicals, dyes, pigments, polymers, and other specialty chemicals. ¹

Applications

Synthesis of high-performance resins

2,2'-bis(trifluoromethyl)benzidine was utilized as a monomer in the synthesis of thermoplastic polyimide (TPI) in combination with 2,3,3',4'-biphenyltetracarboxylic dianhydride and 4,4'-oxydianiline. The TPI was then used in the production of semi-interpenetrating polymer networks (semi-IPNs) by dissolving in bisphenol A dicyanate and curing at elevated temperatures. TPI was found to accelerate the curing reactions of BADCy, resulting in lower curing temperatures and shorter gelation time. SEM images showed that continuous TPI phases were formed in semi-IPNs with a TPI content of 15% and 20%. The resulting semi-IPNs exhibited improved mechanical and dielectric properties compared to pure polycyanurate, with impact strength being 47%-320% greater than that of polycyanurate. The semi-IPNs also maintained comparable or slightly higher thermal resistance compared to polycyanurate. These findings indicate that TPI/BADCy blends have potential for use as high-performance matrix resins for composites and adhesives. ²

Adsorption of pollutants

2,2'-Bis(trifluoromethyl)benzidine has found application in the adsorption of pollutants, particularly aflatoxins. A novel fluorine-functionalized triazine-based porous organic polymer (F-POP) was synthesized by condensation polymerization of TFMB and cyanuric chloride. F-POP, possessing fluorine (F) and imine groups (-NH-), demonstrated excellent adsorption capacity for aflatoxins, surpassing fluorine-free porous organic polymers. The superior performance of F-POP can be attributed to various interaction mechanisms, including hydrogen bonding, F-O interaction, π-π interaction, F-π interaction, and hydrophobic interaction. To enhance its practical utility, magnetic F-POP was prepared by incorporating Fe3O4 nanoparticles into F-POP, enabling magnetic separation. This magnetic sorbent was successfully employed for the extraction of trace amounts of aflatoxins from peanut and rice samples, followed by high-performance liquid chromatography-fluorescence detection. The optimized method displayed high sensitivity, with limits of detection ranging from 0.005 to 0.15 ng g-1. Furthermore, F-POP exhibited exceptional adsorption capabilities towards various pollutants, highlighting its potential for broader applications in pollutant removal and environmental remediation. ³

Safety

2,2'-Bis(trifluoromethyl)benzidine is a highly toxic and potentially carcinogenic compound that poses a significant risk to human health. Exposure to this substance can cause irritation to the eyes, skin, and respiratory system. Long-term exposure may increase the risk of developing cancer. Therefore, it is crucial to take appropriate safety measures when working with this compound, such as wearing protective clothing, ensuring proper ventilation, and avoiding direct contact with skin and eyes. Additionally, thorough toxicological studies are necessary to assess its potential risks and hazards accurately. Overall, the safe handling and usage of 2,2'-Bis(trifluoromethyl)benzidine require strict adherence to relevant regulations and guidelines to minimize the risk of harm to human health. ⁴

Reference

1. PubChem. Compound Summary: 2,2'-Bis(trifluoromethyl)benzidine. National Library of Medicine, 2005.

2. Liu J, Fan W, Lu G, Zhou D, Wang Z, Yan J. Semi-Interpenetrating Polymer Networks Based on Cyanate Ester and Highly Soluble Thermoplastic Polyimide. Polymers (Basel), 2019, 11(5):862.

3. Li J, Yang Y, Zhou Z, Li S, Hao L, Liu W, Wang Z, Wu Q, Wang C. Fluorine-Functionalized Triazine-Based Porous Organic Polymers for the Efficient Adsorption of Aflatoxins. J Agric Food Chem, 2023, 71(6):3068-3078.

4. 2,2'-Bis(trifluoromethyl)benzidine Safety Data Sheets. Echemi, 2019.

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