3-CARBOXYPROPYL DISULFIDE

• A precursor to produce novel polythioester (PTE).
• A reactant in the production of chemically crosslinked epoxidized natural rubber.
• An alternative monolayer for protein chips.

DL-homocysteine (0.300 g, 2.22 mmol) and -thiobutyrolactone (0.576 mL, 6.66 mmol, 3 eq.) were dissolved in a solution of 5 M hydrochloric acid (20 mL) and stirred for 60 hr. at room temperature under an argon atmosphere, and then peroxides (30% aqueous, 0.454 mL, 2 eq.) were added. a white precipitate was observed after 10 min. formation and the reaction was allowed to proceed overnight (TLC). The reaction mixture was then co-evaporated with water three times.

The residue was treated with water (20 mL) and the insoluble solids were filtered out and dried with P2O5 to give the product 3-carboxypropyl disulfide as a white solid (0.523 g, 66%).