Thiosemicarbazide

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.[1] 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.

Thiosemicarbazide
Names
Other names
hydrazinecarbothioamide, N-aminothiourea, aminothiourea
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.077
EC Number
  • 201-184-7
UNII
UN number 2811 2771
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
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

According to X-ray crystallography, the CSN3 core of the molecule is planar as are the three H's nearest the thiocarbonyl group.[2]

Reactions

Thiosemicarbazides are precursors to thiosemicarbazones. They are precursors to heterocycles.[3] Formylation of thiosemicarbazide provides access to triazole.[4]

References

  1. 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.
  2. 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.
  3. 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.
  4. C. Ainsworth (1960). "1,2,4-Triazole". Organic Syntheses. 40: 99. doi:10.15227/orgsyn.040.0099.
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