2-Thiouracil: properties, applications and safety

General Description

2-Thiouracil is a heterocyclic compound with unique properties. It exhibits both acidic and basic properties due to the nitrogen and sulfur atoms. Its tautomeric interconversion and similarity to uracil make it valuable in pharmaceutical synthesis, specifically as an antithyroid agent. In biochemical research, it serves as a sulfur donor and aids in studying biological processes. Additionally, it finds applications in materials science as a ligand, forming complexes with transition metal ions for advanced materials development. However, it is important to note that 2-Thiouracil is considered hazardous and potentially carcinogenic, requiring strict safety precautions in handling, storage, and disposal.

Figure 1. Scandium

Properties

2-Thiouracil is a chemical compound belonging to the class of heterocyclic compounds known as thiopyrimidines. It is structurally similar to uracil, with the addition of a sulfur atom at position 2. This modification confers unique properties to 2-Thiouracil. The compound exhibits both acidic and basic properties due to the presence of the nitrogen and sulfur atoms. It has a molecular formula of C4H4N2OS and a molecular weight of 128.15 g/mol. 2-Thiouracil is a white crystalline solid that is sparingly soluble in water but more soluble in organic solvents. One important property of 2-Thiouracil is its ability to undergo tautomeric interconversion. It exists in two tautomeric forms, namely the thione form and the enol form. The thione form predominates under normal conditions, but the enol form can be stabilized in certain environments or under specific reaction conditions. Due to its structural similarity to uracil, 2-Thiouracil is often used as a building block in the synthesis of pharmaceutical compounds, particularly in the development of antithyroid agents. It has been found to inhibit the production of thyroid hormones by interfering with the activity of the enzyme responsible for thyroid hormone synthesis. In conclusion, 2-Thiouracil possesses unique properties attributed to its thiopyrimidine structure. Its tautomeric interconversion and potential applications in medicinal chemistry make it a valuable compound in various research fields. ¹

Applications

2-Thiouracil, also known as 2-thioxo-4-imidazolidinone, is a versatile compound that finds various applications in different fields.  This chemical compound is derived from uracil and contains a sulfur atom at the 2 position.  In the pharmaceutical industry, 2-Thiouracil has been extensively studied for its potential as an antithyroid agent.  It has been found to inhibit the production of thyroid hormones by interfering with the activity of the enzyme thyroperoxidase.  This property makes it useful in the treatment of hyperthyroidism, a condition characterized by an overactive thyroid gland.  Furthermore, 2-Thiouracil has been utilized in biochemical research as a sulfur donor.  It can be used to study the role of sulfur in various biological processes, including protein structure and function.  Additionally, it has been employed in the synthesis of labeled nucleotides for DNA sequencing and other genetic studies.  Moreover, 2-Thiouracil has found applications in the field of materials science.  It has been employed as a ligand in coordination chemistry, forming complexes with transition metal ions.  These complexes exhibit interesting magnetic and optical properties, making them useful in the development of advanced materials such as sensors and catalysts.  In conclusion, 2-Thiouracil demonstrates diverse applications, ranging from pharmaceuticals to biochemical research and materials science.  Its antithyroid properties, sulfur donation capability, and use as a ligand in coordination chemistry make it a valuable compound in various scientific and industrial endeavors. ²

Safety

2-Thiouracil is considered hazardous and potentially carcinogenic. It falls under Carcinogenicity Category 2 according to the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200), indicating that it is suspected of causing cancer. Safety precautions should be taken when handling 2-Thiouracil. It is important to obtain special instructions before use and to fully understand all safety precautions. Personal protective equipment should be used as required to minimize exposure. Storage of 2-Thiouracil should be done in a locked-up manner to prevent unauthorized access. Disposal of the chemical should be carried out according to proper protocols, preferably through an approved waste disposal plant. In conclusion, due to its potential carcinogenicity and hazardous nature, proper precautions, including obtaining instructions, using personal protective equipment, and adhering to storage and disposal guidelines, should be followed when handling 2-Thiouracil. ³

Reference

1.PubChem. COMPOUND SUMMARY: 2-Thiouracil. National Library of Medicine, 2005. CID: 1269845.

2.Alcolea Palafox M, Franklin Benial AM, K Rastogi V. Biomolecules of 2-Thiouracil, 4-Thiouracil and 2,4-Dithiouracil: A DFT Study of the Hydration, Molecular Docking and Effect in DNA:RNAMicrohelixes. Int J Mol Sci. 2019 Jul 15;20(14):3477.

3.SAFETY DATA SHEET: 2-Thiouracil. Thermo Fisher SCIENTI FIC, 2010.