A novel degradable inimer for atom transfer radical polymerization (ATRP), 2-(6-(2-((2-bromo-2-methylpropanoyl) oxy) ethyl) pyridin-2-yl) ethyl methacrylate (PyDEBrMA), was synthesized by the two-step esterification of 2,6-pyridinediethanol, first with a-bromoisobutyryl bromide in order to introduce the initiator moiety, and then with methacryloyl chloride in order to introduce the monomer moiety. PyDEBrMA was subsequently used to initiate the self-condensing ATRP of methyl methacrylate (MMA) to obtain a hyperbranched MMA homopolymer which could be cleaved at the PyDEBrMA residue either by treatment under mildly alkaline hydrolysis conditions sodium deuteroxide in d(6)-DMSO at room temperature) or thermolysis at 150 degrees C. The lability of the PyDEBrMA residue arises from the presence in its structure of two 2-(pyridin-2-yl) ethyl ester moieties. (C) 2017 Wiley Periodicals, Inc.