Methacryloyl chloride

Tryptone and yeast extract were purchased from Suzhou Biogene Biotechnology Co.,Ltd. Graphite powder, sulfuric acid (H₂SO₄), hydrochloric acid (HCl), hydrogen peroxide (H₂O₂), dimethylacetamide (DMAC), triethylamine (TEA), methacryloyl chloride (MAC), azobisisobutyronitrile (AIBN), methacrylic acid (MAA), butyl methacrylate (BMA), N-hydroxy succinimide (NHS), N,N’-Dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), cyclohexanone, petroleum ether, ether and inorganic salts were all in analytical reagent grade were commercially obtained from Sinopharm Chemical Reagent Co.,Ltd. and used as received without further treatment. HPLC grade methanol was purchased from Shanghai Qiangshun Chemical Reagent Co.,Ltd. HPLC grade DMF was obtained from Tedia Company Inc.

Selenocysteamine hydrochloride (1.0 g, 3.1 mmol, Shanghai Bide Pharmaceutical Technology Co.) was added to 60 mL of anhydrous dichloromethane (J&K Scientific Ltd.) solution and triethylamine (2.5 g, 25.1 mmol) was added under magnetic stirring. After cooling the mixture to 0 °C, methacryloyl chloride (1.3 g, 104.5 mmol, Sinopharm Chemical Reagent Co., Ltd.) was slowly added to the mixture. The reaction mixture was then stirred for 24 h at room temperature under the N₂ atmosphere. After the reaction, the reaction system was extracted with deionised water to remove impurities, dried overnight over anhydrous sodium sulfate (Na₂SO₄, Sinopharm Chemical Reagent Co., Ltd.) and the organic phase was removed by distillation under reduced pressure. The resulting product was purified from the raw material by a silica gel column using ethyl acetate (Jiangsu Yonghua Fine Chemical Co., Ltd.)/petroleum ether (Jiangsu Yonghua Fine Chemical Co., Ltd.) (2:1 by volume).

The copper meshes with different mesh sizes were commercially available. Tryptone and yeast extract were commercially get from Suzhou Biogene Biotechnology Co., Ltd. Graphite flake, methacryloyl chloride (MAC), meth acrylic acid (MAA), butyl methacrylate (BMA) was purchased from Sinopharm Chemical Reagent Co., Ltd, and can be used directly without no further processing. HPLC grade methanol was purchased from Shanghai Qiangshun Chemical Reagent Co., Ltd.