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Rhodanine information


Rhodanine[1]
Names
Preferred IUPAC name
2-Sulfanylidene-1,3-thiazolidin-4-one
Other names
2-Thioxo-4-thiazolidinone; 4-Oxo-2-thioxothiazoline
Identifiers
CAS Number
  • 141-84-4 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL224633 checkY
ChemSpider
  • 1013337 checkY
ECHA InfoCard 100.005.005 Edit this at Wikidata
EC Number
  • 205-505-1
KEGG
  • C07280
PubChem CID
  • 1201546
UNII
  • 7O50LKL2G8 checkY
CompTox Dashboard (EPA)
  • DTXSID4026002 Edit this at Wikidata
InChI
  • InChI=1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6) checkY
    Key: KIWUVOGUEXMXSV-UHFFFAOYSA-N checkY
  • InChI=1/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
    Key: KIWUVOGUEXMXSV-UHFFFAOYAP
SMILES
  • O=C1NC(=S)SC1
Properties
Chemical formula
C3H3NOS2
Molar mass 133.18 g·mol−1
Density 0.868 g/cm−3[2]
Melting point 170 °C (338 °F; 443 K)[2]
Solubility in water
Soluble[2]
Solubility Ethanol, dimethyl sulfoxide[2]
Hazards
GHS labelling:
Pictograms
GHS05: CorrosiveGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H302, H318
Precautionary statements
P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Rhodanine is a 5-membered heterocyclic organic compound possessing a thiazolidine core. It was discovered in 1877 by Marceli Nencki who named it "Rhodaninsaure" in reference to its synthesis from ammonium rhodanide (known as ammonium thiocyanate to modern chemists) and chloroacetic acid in water.[3]

Rhodanines can also be prepared by the reaction of carbon disulfide, ammonia, and chloroacetic acid, which proceeds via an intermediate dithiocarbamate.[4]

  1. ^ Rhodanine at Sigma-Aldrich
  2. ^ a b c d Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press. p. 3.512. ISBN 978-1439855119.
  3. ^ Nencki, M. (10 July 1877). "Ueber die Einwirkung der Monochloressigsäure auf Sulfocyansäure und ihre Salze". Journal für Praktische Chemie. 16 (1): 1–17. doi:10.1002/prac.18770160101.
  4. ^ Redemann, C. Ernst; Icke, Roland N.; Alles, Gordon A. (1955). "Rhodanine". Organic Syntheses; Collected Volumes, vol. 3, p. 763.

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