3274. 2,4-Dinitrobenzenesulfenyl Chloride

Nomenclature

CAS number: 528-76-7
C6H3ClN2O4S; mol wt 234.62.
C 30.72%, H 1.29%, Cl 15.11%, N 11.94%, O 27.28%, S 13.67%.

Description and references

Prepd from bis(2,4-dinitrophenyl)disulfide and chlorine in ethylene bromide: Kharasch et al., J. Am. Chem. Soc. 69, 1612 (1947); 72, 1796 (1950); J. Chem. Educ. 33, 585 (1956); from 2,4-dinitrothiophenol and chlorine in benzene: Perold, Snyman, J. Am. Chem. Soc. 73, 2379 (1951); from 2,4-dinitrophenylbenzyl sulfide and sulfuryl chloride in ethylene chloride: Kharasch, Langford, Org. Synth. 44, 47 (1964). Review: Kharasch, Organic Sulfur Compounds vol. 1 (Pergamon Press, New York, 1961) pp 375-396.

Chemical structure

Properties

Yellow crystals from carbon tetrachloride, mp 96°. Sol in glacial acetic acid, methylene chloride, ethylene chloride, trichlorethylene, benzene, xylene. Somewhat less sol in carbon tetrachloride. Insol in ether. Reacts with alc (even in the cold) to produce ethyl 2,4-dinitrobenzenesulfenate.

Use

Analytical reagent for the characterization of organic compds: Kharasch, J. Chem. Educ. 33. 585 (1956); Langford, Lawson, ibid. 34, 510 (1957).