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.[2] 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.
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Names | |
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Preferred IUPAC name Hydrazinecarbothioamide[1] | |
Other names N-Aminothiourea, Aminothiourea | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.077 |
EC Number |
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PubChem CID | |
UNII | |
UN number | 2811 2771 |
CompTox Dashboard (EPA) | |
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Properties | |
CH5N3S | |
Molar mass | 91.13 g·mol−1 |
Appearance | white solid |
Density | 1.465 g/cm3 |
Melting point | 183 °C (361 °F; 456 K) |
Hazards | |
GHS labelling: | |
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Danger | |
H300, H412 | |
P264, P270, P273, P301+P310, P321, P330, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
According to X-ray crystallography, the CSN3 core of the molecule is planar as are the three H's nearest the thiocarbonyl group.[3]
Reactions
Thiosemicarbazides are precursors to thiosemicarbazones. They are precursors to heterocycles.[4] Formylation of thiosemicarbazide provides access to triazole.[5]
References
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