2164. N-Chlorosuccinimide

Nomenclature

CAS number: 128-09-6
1-Chloro-2,5-pyrrolidinedione; succinchlorimide.
C4H4ClNO2; mol wt 133.53.
C 35.98%, H 3.02%, Cl 26.55%, N 10.49%, O 23.96%.

Description and references

Prepn from succinimide: Hirst, Macbeth, J. Chem. Soc. 121, 2169 (1922); Zimmer, Audrieth, J. Am. Chem. Soc. 76, 3856 (1954). Crystal structure: Brown, Acta Crystallogr. 9, 193 (1956); 14, 711 (1961). Toxicity data: Stohlman, Smith, Public Health Rep. 59, 541 (1944).

Chemical structure

Properties

Orthorhombic crystals, mp 150-151°. Odor of chlorine. Acid to litmus (1:50 aq soln). One gram dissolves in about 70 ml water, 150 ml alcohol, 50 ml benzene. Sparingly sol in ether, chloroform, carbon tetrachloride. Liberates iodine from potassium iodide solns, and bromine from sodium bromide solns. MLD orally in rats: 2.7 g/kg (Stohlman, Smith).

Use

Chlorinating agent.