Thiosemicarbazide

Thiosemicarbazide
Names
	Preferred IUPAC name Hydrazinecarbothioamide
	Other names N-Aminothiourea, Aminothiourea
Identifiers
CAS Number	79-19-6;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL256250;
ChemSpider	2005980;
ECHA InfoCard	100.001.077
EC Number	201-184-7;
PubChem CID	2723789;
UNII	6056O8W6ET;
UN number	2811 2771
CompTox Dashboard (EPA)	DTXSID9021346 ;
	InChI InChI=1S/CH5N3S/c2-1(5)4-3/h3H2,(H3,2,4,5) Key: BRWIZMBXBAOCCF-UHFFFAOYSA-N;
	SMILES C(=S)(N)NN;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H300, H412
Precautionary statements	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). 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. p. 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. Bibcode:1970AcCrB..26.1005A. 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. Bibcode:2012RuCRv..81..494G. doi:10.1070/RC2012v081n06ABEH004235. S2CID 96691115.
^ C. Ainsworth (1960). "1,2,4-Triazole". Organic Syntheses. 40: 99. doi:10.15227/orgsyn.040.0099.

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1003. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[2] 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.

[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. Bibcode:1970AcCrB..26.1005A. doi:10.1107/S0567740870003497.

[4] 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. Bibcode:2012RuCRv..81..494G. doi:10.1070/RC2012v081n06ABEH004235. S2CID 96691115.

[5] C. Ainsworth (1960). "1,2,4-Triazole". Organic Syntheses. 40: 99. doi:10.15227/orgsyn.040.0099.

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