• Korean Chemical Engineering Research
• /
• v.49 no.3
• /
• pp.330-337
• /
• 2011

In this research, the preparation processes for making a series of $\omega$-mercapto alkylamine 1 and $\omega$-mercapto alkanoic acid 2 useful for studying of the self-assembled monolayer(SAM) are described. The preparation methods of the first goal materials, $\omega$-mercapto alkylamines 1 were carried out as follows: First, $\omega$-phthalimide alkanol 3 was synthesized from commercially available potassium phthalimide derivatives and $\omega$-bromoalkanol in DMF at $80{^{\circ}C}$ via substitution reaction. After refluxing $\omega$-phthalimide alkanol 3 with hydrazine hydrate in ethanol followed by treating with c-HCl, $\omega$-aminoalkanol 4 was obtained in 76-98% yield, accompanied with side-product 5. Bromination of hydroxyl moiety of $\omega$-aminoalkanol 4 using aqueous hydrobromic acid furnished $\omega$-bromoamine 6 in 34-97% yields. Substitution reaction 6 with thiourea in 95% ethanol gave $\omega$-aminoalkanthiuronium 7, which was treated with aqueous strong base and aqueous strong sulfuric acid gave desired products, $\omega$-mercapto alkylamines 1 through overall 5 steps. The second target material, $\omega$-mercapto alkanoic acid 2 was prepared via 2 steps. $\omega$-bromo alkanoic acid was reacted with thiourea to give $\omega$-thiourea alkanoic acid 7 in 69-85%, which was treated with aqueous strong base and strong acid to furnish $\omega$-mercapto alkanoic acid 2 in 50-98%. The fabricated long-chain alkylthiol(LCAT) can be used as linkers to immobilize protein, enzyme and various kinds of biomolecules on the surface of metallic materials(Au, Pt, Ti) by SAM, and can be useful chemical tools for the application study on the surface modification of metallic materials.