1254. Bis(2-mercaptoethyl)sulfone

Nomenclature

CAS number: 145626-87-5
2,2′-Sulfonylbis(ethanethiol); BMS.
C4H10O2S3; mol wt 186.32.
C 25.79%, H 5.41%, O 17.17%, S 51.63%.

Description and references

Reducing agent for proteins. Prepn: G. V. Lamoureux, G. M. Whitesides, J. Org. Chem. 58, 633 (1993). Enhanced reduction rate in comparison with dithiothreitol, q.v.: R. Singh, G. M. Whitesides, Bioorg. Chem. 22, 109 (1994). Use in reduction of disulfide bonds: D. Winitz et al., J. Biol. Chem. 271, 27645 (1996); A. Brunella, O. Ghisalba, J. Mol. Catal. B 10, 215 (2000); S. Lee, J. P. N. Rosazza, Org. Lett. 6, 365 (2004).

Chemical structure

Properties

White fluffy crystals from hexane, mp 57-58°. pKa (aqueous soln at 25°): 7.9, 9.0. Keq (for the reduction of DTT): 0.35

Use

Reagent for reduction of disulfide bonds in aqueous solutions.