對苯二甲醛
| 對苯二甲醛 | |
|---|---|
| |
| 別名 | 1,4-苯二甲醛 苯-1,4-二甲醛 |
| 識別 | |
| CAS編號 | 623-27-8 
|
| 性質 | |
| 化學式 | C8H6O2 |
| 摩爾質量 | 134.13 g·mol−1 |
| 熔點 | 114—115 °C（387—388 K）[1] |
| 溶解性（水） | 0.11 g（25 °C） |
| 若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。 | |
合成
對苯二甲酸在叔戊酸酐存在下、鈀配合物催化下氫化，可以得到對苯二甲醛；[4]它也可由對苯二甲腈經三(二烷基胺基)氫化鈉還原得到。[5]
2,5-二羥基-1,4-苯二甲醛在二氯甲烷中和三溴化硼反應，也能得到對苯二甲醛。[6]
反應
對苯二甲醛具有醛的通性，如可以和胺縮合，形成C=N-C鍵，並可進一步被硼氫化鈉還原為二級胺（C-NH-C）。[7]它可以發生亨利反應，如和硝基甲烷反應，生成α,α'-二(硝基甲基)對苯二甲醇。[8]它和氰乙酸乙酯發生Knoevenagel縮合反應，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、巴比妥酸等活潑亞甲基化合物[10]的反應也是已知的。在溴化氰和乙醇鈉存在下，它和丙二腈反應，生成1,4-二(2,2,3,3-四氰基環丙基)苯。[11]
在三乙胺催化下，它可以和亞磷酸二甲酯反應，得到(1,4-苯二基)二(羥甲基膦酸二甲酯)。[12]
參考文獻
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