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. 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.