2-[2-(2-methoxyethoxy)ethoxy]-ethanethiol

2-[2-(2-methoxyethoxy)ethoxy]-ethanethiol can be used to prepare biofunctional silicon nanoparticles for drug delivery.

Toluene-4-sulfonic acid 2-[2-(2-methoxyethoxy)-ethoxy]-ethyl ester (2.7) (10.8 g, 34 mmol) and thiourea (2.6 g, 34 mmol) were dissolved in a mixture of absolute EtOH (20 mL) and H2O (14 mL) and the mixture was refluxed for 3h. 4N NaOH solution (10 mL) was added to mixture and the reaction mixture refluxed 2 more h. The reaction mixture was concentrated under reduced pressure to ~ 10 mL, diluted with distilled H2O (10 mL) and neutralized with concentrated HCl. The solution was extracted with CH2Cl2 (3x10mL) and the solvent was evaporated under reduced pressure. The pink-yellow liquid was distilled at 0.45 torr pressure. The product was collected as a clear liquid and obtained in 54% yield. B.p. 55-57 °C at 0.45 torr. GC-MS Calcd. C7H16O3S+ : 180.0; found: 179.9. 1 H NMR (250 MHz, CDCl3) δ 3.6(6H), 3.5(4H), 3.4(3H), 2.7(2H), 1.6(1H); 13 C NMR (300 MHz, CDCl3) δ 76.92, 73.30, 72.34, 70.98, 70.63, 59.46, 24.66