Bis(2-mercaptoethyl)sulfone

Title: Bis(2-mercaptoethyl)sulfone
CAS Registry Number: 145626-87-5
CAS Name: 2,2¢-Sulfonylbis(ethanethiol)
Additional Names: BMS
Molecular Formula: C4H10O2S3
Molecular Weight: 186.32
Percent Composition: C 25.79%, H 5.41%, O 17.17%, S 51.63%
Literature 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).
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
Melting point: mp 57-58°
pKa: pKa (aqueous soln at 25°): 7.9, 9.0
Use: Reagent for reduction of disulfide bonds in aqueous solutions.
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