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对苯二甲醛

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对苯二甲醛
别名 1,4-苯二甲醛
苯-1,4-二甲醛
识别
CAS号 623-27-8  checkY
性质
化学式 C8H6O2
摩尔质量 134.13 g·mol−1
熔点 114—115 °C(387—388 K)[1]
溶解性 0.11 g(25 °C)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

对苯二甲醛是一种有机化合物,化学式为C8H6O2

合成

对苯二甲醛可由对苯二甲醇的催化氧化反应制得。[2][3]

对苯二甲酸在叔戊酸酐存在下、钯配合物催化下氢化,可以得到对苯二甲醛;[4]它也可由对苯二甲腈经三(二烷基氨基)氢化钠还原得到。[5]

2,5-二羟基-1,4-苯二甲醛在二氯甲烷中和三溴化硼反应,也能得到对苯二甲醛。[6]

反应

对苯二甲醛具有的通性,如可以和胺缩合,形成C=N-C键,并可进一步被硼氢化钠还原为仲胺(C-NH-C)。[7]它可以发生亨利反应,如和硝基甲烷反应,生成α,α'-二(硝基甲基)对苯二甲醇。[8]它和氰乙酸乙酯发生Knoevenagel缩合反应,生成3,3'-(1,4-苯二基)二(2-氰基-2-丙烯酸乙酯)。[9]

除了氰乙酸乙酯外,它和丙二腈丙二酸二乙酯巴比妥酸等活泼亚甲基化合物[10]的反应也是已知的。在溴化氰乙醇钠存在下,它和丙二腈反应,生成1,4-二(2,2,3,3-四氰基环丙基)苯。[11]

三乙胺催化下,它可以和亚磷酸二甲酯反应,得到(1,4-苯二基)二(羟甲基膦酸二甲酯)。[12]

参考文献

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  5. ^ Cha, Jin Soon; Jeoung, Min Kyoo; Kim, Jong Mi; Kwon, Oh Oun; Lee, Jae Cheol. Conversion of Aromatic Nitriles to Aldehydes by Sodium Tris(dialkylamino)aluminum Hydrides. Organic Preparations and Procedures International. October 1994, 26 (5): 583–588 [2022-07-29]. ISSN 0030-4948. doi:10.1080/00304949409458063. eISSN 1945-5453. (原始内容存档于2022-07-29). 
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