Thiosemicarbazide

Last updated
Thiosemicarbazide
Thiosemicarbazide.png
Names
Preferred IUPAC name
Hydrazinecarbothioamide [1]
Other names
N-Aminothiourea, Aminothiourea
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.077 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-184-7
PubChem CID
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
Appearancewhite solid
Density 1.465 g/cm3
Melting point 183 °C (361 °F; 456 K)
Hazards
GHS labelling:
GHS-pictogram-skull.svg
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]

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<span class="mw-page-title-main">Organometallic chemistry</span> Study of organic compounds containing metal(s)

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Gregory S. Girolami is the William H. and Janet G. Lycan Professor of Chemistry at the University of Illinois Urbana-Champaign. His research focuses on the synthesis, properties, and reactivity of new inorganic, organometallic, and solid state species. Girolami has been elected a fellow of the American Association for the Advancement of Science, the Royal Society of Chemistry, and the American Chemical Society.

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. 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.