8184. Rhodanine

Nomenclature

CAS number: 141-84-4
2-Thioxo-4-thiazolidinone; 2-thio-4-ketothiazolidine; 4-oxo-2-thionothiazolidine; rhodanic acid.
C3H3NOS2; mol wt 133.19.
C 27.05%, H 2.27%, N 10.52%, O 12.01%, S 48.15%.

Description and references

Prepd by the action of sodium chloroacetate on ammonium dithiocarbamate: Julian, Sturgis, J. Am. Chem. Soc. 57, 1126 (1935); Redemann et al., Org. Synth. coll. vol. III, 763 (1955).

Chemical structure

Properties

Pale yellow crystals (long blades) from glacial acetic acid or water. d 0.868. mp 168.5° (capillary); mp 170.5-171° (hot stage). May explode on rapid heating. pK (25°) 5.52. Freely sol in boiling water, in methanol, ethanol, DMF, ether, alkalies, ammonia, hot acetic acid.

Use

In the synthesis of phenylalanine.