氯乙醛是一种有机化合物,结构式ClCH2CHO。它是无色具刺鼻辛辣气味的液体,也是强亲电试剂和危险的烷基化试剂。氯乙醛通常不以无水物存在,而是以半缩水合醛(ClCH2CH(OH))2O形式存在。它可用于有机合成。
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氯乙醛是抗肿瘤药异环磷酰胺的代谢产物,被认为是异环磷酰胺某些毒性的来源。[10]氯乙醛也是氯乙烯和1,2-二氯乙烷的代谢产物。[11]它会腐蚀粘膜及刺激眼睛、皮肤和呼吸道。[2]
把乙醛或三聚乙醛氯化能得到氯乙醛[2]。反应也会产生二氯乙醛和三氯乙醛[12],而这三者都是乙烯通过瓦克尔法转化成乙醛时产生的副产物。[12]无水氯乙醛可由高碘酸盐氧化3-氯-1,2-丙二醇而成。[5][13]氯乙醛还能通过氯乙烯和氯水的反应产生:[12]
- ClCH=CH2 + Cl2 + H2O → ClCH2CHO + 2 HCl
除此之外,氯乙醛还可以通过一氯代碳酸乙烯酯的分解产生。[12][14]
无水氯乙醛在室温下容易聚合成三聚体、四聚体或多聚体。[12]氯乙醛也会和水反应,生成缩醛半水合物1,1'-二羟基-2,2'-二氯乙醚。[12]这种化合物是无色晶体,熔点43-50 °C,沸点84 °C,并分解成氯乙醛和水。[12]
这种半水合物可被浓硫酸脱水,生成三聚氯乙醛(2,4,6-三(氯甲基)-1,3,5-三𫫇烷)。[12][15]它是无色晶体,熔点88–89 °C。[12]
半水合物通过共沸蒸馏脱水得到的是四聚氯乙醛(2,4,6,8-四(氯甲基)-1,3,5,7-四氧杂环辛烷)。[16][12]和三聚体一样,它也是无色晶体,熔点65–67 °C。[12]
用硝酸或过氧化氢等氧化剂氧化氯乙醛可以得到氯乙酸。[12]
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