对苯二甲醛
| 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 
|
| 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（水） | 0.11 g（25 °C） |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
合成
[编辑]
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
[编辑]对苯二甲醛具有醛的通性，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。在溴化氰和乙醇钠存在下，它和丙二腈反应，生成1,4-二(2,2,3,3-四氰基环丙基)苯。[11]
在三乙胺催化下，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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