Rhodanine

Not to be confused with rhodamine.
Rhodanine[1]
Names
Preferred IUPAC name
2-Sulfanylidene-1,3-thiazolidin-4-one
Other names
2-Thioxo-4-thiazolidinone; 4-Oxo-2-thioxothiazoline
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.005 Edit this at Wikidata
EC Number
  • 205-505-1
KEGG
UNII
  • 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
  • O=C1NC(=S)SC1
Properties
C3H3NOS2
Molar mass 133.18 g·mol−1
Density 0.868 g/cm−3[2]
Melting point 170 °C (338 °F; 443 K)[2]
Soluble[2]
Solubility Ethanol, dimethyl sulfoxide[2]
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H318
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).
checkY verify (what is checkY☒N ?)

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.