Bis(2-mercaptoethyl) sulfone

Chemical Properties

White Crystalline Solid

Uses

Bis(2-mercaptoethyl) sulfone is a useful reagent for the reduction of disulfides in aquous solutions. It is a superior substitute for DTT.

Uses

Reagent for reduction of disulfide bonds in aqueous solutions.

Purification Methods

BMS recrystallises from hexane as white fluffy crystals. Large amounts are best recrystallised from de-oxygenated H2O (charcoal). It is a good alternative reducing agent to dithiothreitol. Its IR (film) has 2995, 2657, 1306, 1248, 1124 and 729 cm-1 . The synthetic intermediate thioacetate has m 82-83o (white crystals from CCl4). The disulfide is purified by flash chromatography on SiO2 and elution with 50% EtOAc/hexane and recrystallised from hexane, and has m 137-139o. [Lamoureux & Whitesides J Org Chem 58 633 1993, Beilstein 1 IV 2455.]