4646. Hemisulfur Mustard

Nomenclature

CAS number: 693-30-1
2-[(2-Chloroethyl)thio]ethanol; 2-chloro-2′-hydroxydiethyl sulfide; 2-chloroethyl 2-hydroxyethyl sulfide; β-chloroethyl β-hydroxyethyl thioether; mustard chlorohydrin; semi-mustard gas; semisulfur mustard.
C4H9ClOS; mol wt 140.63.
C 34.16%, H 6.45%, Cl 25.21%, O 11.38%, S 22.80%.

Description and references

Prepn: Ogston et al., Trans. Faraday Soc. 44, 45 (1948); Grant, Kinsey, J. Am. Chem. Soc. 68, 2075 (1946); Fuson, Ziegler, J. Org. Chem. 11, 510 (1946); Rueggeberg et al., ibid. 13, 110 (1948); Tsou et al., ibid. 26, 4987 (1961).

Chemical structure

Properties

Oily, somewhat hygroscopic liquid. bp0.6 100° (Fuson); bp0.5-0.75 87°; bp6 44.5° (Rueggeberg). nD20 1.5188; nD24.5 1.5205. Sol in water; miscible with bis(2-chloroethyl) sulfide, thiodiglycol. Unstable, forming sulfonium salts at room temp or in solns with ethanol or chloroform.