Chemistry:Thiosemicarbazide
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| Names | |
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| Preferred IUPAC name
Hydrazinecarbothioamide[1] | |
| Other names
N-Aminothiourea, Aminothiourea
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| EC Number |
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PubChem CID
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| UNII | |
| UN number | 2811 2771 |
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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 pictograms | 
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| GHS Signal word | Danger |
| H300, H412 | |
| P264, P270, P273, P301+310, P321, P330, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
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.
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
- ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 1003. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ↑ Campbell, Michel J.M. (1975). "Transition metal complexes of thiosemicarbazide and thiosemicarbazones". Coordination Chemistry Reviews 15 (2–3): 279–319. doi:10.1016/S0010-8545(00)80276-3.
- ↑ Andreetti, G. D.; Domiano, P.; Gasparri, G. F.; Nardelli, M.; Sgarabotto, P. (1970). "Hydrogen bonding in thiosemicarbazide". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry 26 (7): 1005–1009. doi:10.1107/S0567740870003497.
- ↑ Gazieva, Galina A.; Kravchenko, Angelina N. (2012). "Thiosemicarbazides in the synthesis of five- and six-membered heterocyclic compounds". Russian Chemical Reviews 81 (6): 494–523. doi:10.1070/RC2012v081n06ABEH004235. Bibcode: 2012RuCRv..81..494G.
- ↑ C. Ainsworth (1960). "1,2,4-Triazole". Organic Syntheses 40: 99. doi:10.15227/orgsyn.040.0099.
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