Thiosemicarbazide
Names
Preferred IUPAC name
Hydrazinecarbothioamide[1]
Other names
N-Aminothiourea, Aminothiourea
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.077 Edit this at Wikidata
EC Number
  • 201-184-7
UNII
UN number 2811 2771
  • InChI=1S/CH5N3S/c2-1(5)4-3/h3H2,(H3,2,4,5)
    Key: BRWIZMBXBAOCCF-UHFFFAOYSA-N
  • C(=S)(N)NN
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:
GHS06: Toxic
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).

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

  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. 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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