氯乙醛是一種有機化合物,結構式ClCH2CHO。它是無色具刺鼻辛辣氣味的液體,也是強親電試劑和危險的烷基化試劑。氯乙醛通常不以無水物存在,而是以半縮水合醛(ClCH2CH(OH))2O形式存在。它可用於有機合成。
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氯乙醛是抗腫瘤藥異環磷醯胺的代謝產物,被認為是異環磷醯胺某些毒性的來源。[10]氯乙醛也是氯乙烯和1,2-二氯乙烷的代謝產物。[11]它會腐蝕黏膜及刺激眼睛、皮膚和呼吸道。[2]
把乙醛或三聚乙醛氯化能得到氯乙醛[2]。反應也會產生二氯乙醛和三氯乙醛[12],而這三者都是乙烯通過瓦克爾法轉化成乙醛時產生的副產物。[12]無水氯乙醛可由高碘酸鹽氧化3-氯-1,2-丙二醇而成。[5][13]氯乙醛還能通過氯乙烯和氯水的反應產生:[12]
- ClCH=CH2 + Cl2 + H2O → ClCH2CHO + 2 HCl
除此之外,氯乙醛還可以通過一氯代碳酸乙烯酯的分解產生。[12][14]
無水氯乙醛在室溫下容易聚合成三聚體、四聚體或多聚體。[12]氯乙醛也會和水反應,生成縮醛半水合物1,1'-二羥基-2,2'-二氯乙醚。[12]這種化合物是無色晶體,熔點43-50 °C,沸點84 °C,並分解成氯乙醛和水。[12]
這種半水合物可被濃硫酸脫水,生成三聚氯乙醛(2,4,6-三(氯甲基)-1,3,5-三噁烷)。[12][15]它是無色晶體,熔點88–89 °C。[12]
半水合物通過共沸蒸餾脫水得到的是四聚氯乙醛(2,4,6,8-四(氯甲基)-1,3,5,7-四氧雜環辛烷)。[16][12]和三聚體一樣,它也是無色晶體,熔點65–67 °C。[12]
用硝酸或過氧化氫等氧化劑氧化氯乙醛可以得到氯乙酸。[12]
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