Thiosemicarbazide is the chemical compound with the formula H2NC(S)NHNH2. A white, odorless solid, it is related to thiourea (H2NC(S)NH2) by the insertion of an NH center. They are commonly used as ligands for transition metals. Many thiosemicarbazides are known. These feature an organic substituent in place of one or more H's of the parent molecule. 4-Methyl-3-thiosemicarbazide is a simple example. According to X-ray crystallography, the CSN3 core of the molecule is almost planar as are the three H atoms nearest the thiocarbonyl group. This can be explained by models of electron delocalisation.
Reactions Thiosemicarbazides are precursors to thiosemicarbazones. They are precursors to heterocycles. Formylation of thiosemicarbazide provides access to triazole.
Applications Some of the known uses of thiosemicarbazide include in the synthesis of: Nicothiazone, Methisazone, Tegaserod, Isobuzole, Ambazone & Citenazone.
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