對苯二甲醛
外觀
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對苯二甲醛 | |
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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
[編輯]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
[編輯]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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- ^ Nagayama, Kazuhiro; Shimizu, Isao; Yamamoto, Akio. Direct Hydrogenation of Carboxylic Acids to Corresponding Aldehydes Catalyzed by Palladium Complexes in the Presence of Pivalic Anhydride. Chemistry Letters. November 1998, 27 (11): 1143–1144 [2022-07-29]. ISSN 0366-7022. doi:10.1246/cl.1998.1143. eISSN 1348-0715. (原始內容存檔於2022-07-29).
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