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對苯二甲醛

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對苯二甲醛
別名 1,4-苯二甲醛
苯-1,4-二甲醛
識別
CAS號 623-27-8  checkY
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 0.11 g(25 °C)
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

對苯二甲醛是一種有機化合物,化學式為C8H6O2

合成

[編輯]

對苯二甲醛可由對苯二甲醇的催化氧化反應製得。[2][3]

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(二烷基氨基)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仲胺(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]

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

[編輯]
  1. ^ Doleschall, Gábor. Novel aldehyde syntheses based on selective reduction of s-triazole derivatives. Tetrahedron. January 1976, 32 (21): 2549–2558. ISSN 0040-4020. doi:10.1016/0040-4020(76)88025-8. 
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  4. ^ 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). 
  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. (原始內容存檔於2022-07-29). 
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  7. ^ Pettersson, Sofia; Pérez-Nueno, Violeta I.; Ros-Blanco, Laia; Puig de La Bellacasa, Raimon; Rabal, María Obdulia; Batllori, Xavier; Clotet, Bonaventura; Clotet-Codina, Imma; Armand-Ugón, Mercedes; Esté, José; Borrell, José I.; Teixidó, Jordi. Discovery of Novel Non-Cyclam Polynitrogenated CXCR4 Coreceptor Inhibitors. ChemMedChem. 20 October 2008, 3 (10): 1549–1557 [2022-07-29]. ISSN 1860-7179. PMID 18671217. doi:10.1002/cmdc.200800145. eISSN 1860-7187. (原始內容存檔於2022-07-29). 
  8. ^ Alizadeh, Abdolhamid; Khodaei, Mohammad M.; Abdi, Gisya; Kordestani, Davood. The First Report on Chemoselective Biguanide-Catalyzed Henry Reaction under Neat Conditions. Bulletin of the Korean Chemical Society. 20 November 2012, 33 (11): 3640–3644 [2022-07-29]. ISSN 0253-2964. doi:10.5012/bkcs.2012.33.11.3640. (原始內容存檔於2022-07-29). 
  9. ^ Kühbeck, Dennis; Saidulu, G.; Reddy, K. Rajender; Díaz, David Díaz. Critical assessment of the efficiency of chitosan biohydrogel beads as recyclable and heterogeneous organocatalyst for C–C bond formation. Green Chem. 2012, 14 (2): 378–392 [2022-07-29]. ISSN 1463-9262. doi:10.1039/C1GC15925A. eISSN 1463-9270. (原始內容存檔於2022-07-29). 
  10. ^ Siddiqui, Zeba N.; Khan, Tabassum. Sulfuric acid-modified PEG-6000 (PEG–OSO3H): a biodegradable, reusable solid acid catalyst for highly efficient and eco-friendly synthesis of novel bis-Knoevenagel products under solvent-free conditions. Tetrahedron Letters. July 2013, 54 (29): 3759–3764. ISSN 0040-4039. doi:10.1016/j.tetlet.2013.05.012. 
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