10329. N-Chlorosaccharin

Nomenclature

CAS number: 14070-51-0
2-Chloro-1,2-benzisothiazol-3(2H)-one 1,1-dioxide; o-benzoic N-chlorosulphinide; NCSA; NCSac.
C7H4ClNO3S; mol wt 217.63.
C 38.63%, H 1.85%, Cl 16.29%, N 6.44%, O 22.05%, S 14.73%.

Description and references

Reagent that is a source of electrophilic chlorine; utilized for a variety of chlorination and oxidation reactions. Prepn: F. D. Chattaway, J. Chem. Soc. Trans. 87, 1882 (1905) DOI. Green prepn: S. P. L. de Souza et al., Synth. Commun. 33, 935 (2003) DOI. Stability and chlorine potential studies: H.-S. Dawn et al., J. Pharm. Sci. 59, 955 (1970) DOI PubMed. Synthetic applications: J. M. Bachhawat et al., Indian J. Chem. 11, 609 (1973); D. Dolenc, B. Sket, Synlett 1995, 327 DOI; N. Iranpoor et al., Can. J. Chem. 84, 69 (2006) DOI. Oxidimetric titration studies: N. Jayasree, P. Indrasenan, Indian J. Chem. 26A, 714 (1987). Review: P. E. Gama, Synlett 2008, 1742-1743 DOI.

Chemical structure

Properties

White crystalline powder, mp 152°. Crystallizes into long, flattened prisms from chloroform, acetic acid. Peculiar odor resembles chloral hydrate. Dec slowly with evolution of gas when heated above 260°. Soly at 25° (g/l): 1,4-dioxane 287.0; acetone 173.0; chloroform 112.0; ethyl acetate 81.1; carbon tetrachloride 4.3; water ≈0.1; at 30° (g/l): acetic acid 44.83.

Use

Reagent in synthetic organic chemistry. Titrant in analytical chemistry.