Thiosemicarbazide

{{Chembox

| ImageFile = Thiosemicarbazide.png

| ImageSize =

| ImageAlt =

| PIN = Hydrazinecarbothioamide{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=1003 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}

| OtherNames = N-Aminothiourea, Aminothiourea

|Section1={{Chembox Identifiers

| CASNo = 79-19-6

| PubChem = 2723789

| EC_number = 201-184-7

| UNNumber = 2811 2771

| UNII = 6056O8W6ET

| ChEMBL = 256250

| ChemSpiderID = 2005980

| StdInChI=1S/CH5N3S/c2-1(5)4-3/h3H2,(H3,2,4,5)

| StdInChIKey = BRWIZMBXBAOCCF-UHFFFAOYSA-N

| SMILES = C(=S)(N)NN

}}

|Section2={{Chembox Properties

| C=1|S=1|N=3|H=5

| MolarMass =

| Appearance = white solid

| Density = 1.465 g/cm³

| MeltingPtC = 183

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS06}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|300|412}}

| PPhrases = {{P-phrases|264|270|273|301+310|321|330|405|501}}

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

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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.{{cite journal|doi=10.1016/S0010-8545(00)80276-3|title=Transition metal complexes of thiosemicarbazide and thiosemicarbazones|year=1975|last1=Campbell|first1=Michel J.M.|journal=Coordination Chemistry Reviews|volume=15|issue=2–3|pages=279–319}} 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.{{cite journal |doi=10.1107/S0567740870003497|title=Hydrogen bonding in thiosemicarbazide|year=1970|last1=Andreetti|first1=G. D.|last2=Domiano|first2=P.|last3=Gasparri|first3=G. F.|last4=Nardelli|first4=M.|last5=Sgarabotto|first5=P.|journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry|volume=26|issue=7|pages=1005–1009|bibcode=1970AcCrB..26.1005A }} This can be explained by models of electron delocalisation.