Rhodanine

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.

Not to be confused with rhodamine.
Rhodanine
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
EC Number
  • 205-505-1
KEGG
UNII
  • InChI=1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6) Y
    Key: KIWUVOGUEXMXSV-UHFFFAOYSA-N Y
  • 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
Melting point 170 °C (338 °F; 443 K)
Soluble
Solubility Ethanol, dimethyl sulfoxide
Hazards
GHS labelling:
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).
Y verify (what is YN ?)
Infobox references

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

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