My aim is to develop a polymer brush on a glass surface, for that I will first functionalize with 3-CHLOROPROPYLTRIMETHOXYSILANE my glass slides.
As a final product I need to replace the ending CL for a -O-NH2.
Any suggestions in how can I achieve that?
http://www.sigmaaldrich.com/catalog/product/aldrich/440183?lang=en®ion=GB
This is not easy because alkylation of hydroxyamine results in every case in a mixture of O- and N-alkylated products. If you can live with such a mixture you can try to make the reaction in solvents like acetonitrile in presence of equimolar amounts of a strong organic base like DBU. If you want to get exclusively the O-alkylated product you must protect the NH groups e.g. by oxime or with the BOC protecting group but in both cases you have the problem to deprotect the product afterwards without hydrolysing the methoxysilyl groups.
A complete different strategy is to make a hydrosilylation of O-allyl hydroxylamine whose hydrochloride can be bought from SIGMAALDRICH.
SiH(OR)3 + H2C=CH-CH2-O-NH2 -> (RO)3Si-CH2-CH2-CH2-O-NH2
Some ppm of Pt hydrosilylation catalysts (available also from SIGMAALDRICH) must be used for this reaction which proceed generally in quantitative yields.
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