General Description

1,1'-Thiocarbonyldiimidazole is a highly reactive and versatile compound used in organic synthesis. Its reactivity towards nucleophiles makes it valuable in the preparation of various chemical compounds. It is stable, easily handled, and soluble in common organic solvents, enhancing its applicability in laboratory settings. In analytical chemistry, it finds applications in the determination of plasma cysteine and homocysteine levels using capillary electrophoresis. Safety protocols should be followed when handling 1,1'-Thiocarbonyldiimidazole to prevent potential hazards. Overall, this compound serves as an essential reagent in organic synthesis and offers a valuable tool for accurate analyses in clinical and biomedical research.

Figure 1. 1,1'-Thiocarbonyldiimidazole

Properties

1,1'-Thiocarbonyldiimidazole is an organic compound with a molecular formula of C9H6N4S. It is a versatile and widely used reagent in organic synthesis due to its unique properties. One of the key properties of 1,1'-Thiocarbonyldiimidazole is its high reactivity towards nucleophiles, such as amines and alcohols. It readily reacts with these compounds to form corresponding thiourea derivatives or carbamates, respectively. This property makes 1,1'-Thiocarbonyldiimidazole useful in various synthetic processes, including the preparation of pharmaceuticals, agrochemicals, and polymers. 1,1'-Thiocarbonyldiimidazole is also known for its stability and ease of handling. It is a solid, crystalline compound that can be stored and transported without significant decomposition. Its stability allows for long-term storage and use in various laboratory settings. Furthermore, 1,1'-Thiocarbonyldiimidazole exhibits good solubility in common organic solvents, such as dichloromethane and tetrahydrofuran, which enhances its applicability in solution-based reactions. In summary, 1,1'-Thiocarbonyldiimidazole is a highly reactive compound that finds wide utility in organic synthesis. Its ability to react with nucleophiles, stability, and solubility make it an essential reagent in the preparation of diverse chemical compounds. ¹

Applications

1,1'-Thiocarbonyldiimidazole has found various applications in analytical chemistry, particularly in the determination of total plasma cysteine and homocysteine using capillary electrophoresis. This method offers a simple and rapid approach for analyzing these compounds in human plasma samples. To perform the analysis, the plasma samples are first reduced with dithiothreitol to prepare them for further processing. Subsequently, 1,1'-Thiocarbonyldiimidazole in acetonitrile is used to react with the plasma samples. After centrifugation, the resulting supernatant is directly injected into a capillary, where analytes are stacked through alkaline post-injection. By utilizing a 50μm i.d. silica capillary with specific buffer conditions (0.1M triethanolamine, 0.15M formic acid, and 50μM hexadecyltrimethylammonium bromide at pH 3.9), the method achieves a limit of quantification of 2.5μM for homocysteine. The accuracy ranges from 94.7% to 105.1%, while the intra- and inter-day imprecisions are below 2.5% and 3%, respectively. Notably, the entire analysis can be completed within a short duration of 6 minutes. Additionally, the sensitivity of the method can be significantly enhanced by employing liquid-phase extraction with isopropanol, leading to a fourfold increase in sensitivity. These applications of 1,1'-Thiocarbonyldiimidazole in capillary electrophoresis provide a valuable tool for the efficient and accurate determination of total plasma cysteine and homocysteine levels, benefiting clinical and biomedical research. ²

Safety

1,1'-Thiocarbonyldiimidazole is a chemical reagent commonly used in organic synthesis and materials science. When handling 1,1'-Thiocarbonyldiimidazole, it is crucial to adhere to strict safety protocols to prevent potential hazards. First and foremost, personal protective equipment (PPE) such as gloves, lab coats, and safety goggles should be worn at all times when working with 1,1'-Thiocarbonyldiimidazole to prevent skin and eye contact. In addition, 1,1'-Thiocarbonyldiimidazole should only be used in a well-ventilated area or in a fume hood to minimize inhalation exposure. It is important to avoid ingestion of TCDI, and thorough handwashing is essential after handling the compound. Furthermore, 1,1'-Thiocarbonyldiimidazole should be stored in a cool, dry place away from direct sunlight and incompatible substances. It is sensitive to moisture and should be kept tightly sealed when not in use to prevent decomposition. In case of accidental exposure or spillage, appropriate measures for chemical cleanup and disposal should be followed according to established safety guidelines and regulations. By following these safety precautions, the risk associated with handling 1,1'-Thiocarbonyldiimidazole can be effectively minimized, ensuring a safe working environment for laboratory personnel. ³

Reference

1. PubChem. COMPOUND SUMMARY: 1,1'-Thiocarbonyldiimidazole. National Library of Medicine, PubChem CID: 80264.

2. Ivanov AV, Virus ED, Luzyanin BP, Kubatiev AA. Capillary electrophoresis coupled with 1,1'-thiocarbonyldiimidazole derivatization for the rapid detection of total homocysteine and cysteine in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Nov 1;1004:30-36.

3. 1,1'-thiocarbonylbis(imidazole). European Chemicals Agency, EC / List no. 228-183-4.