4-氯吡啶
外觀
4-氯吡啶 | |
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英文名 | 4-chloropyridine |
別名 | 對氯吡啶 p-氯吡啶 |
識別 | |
CAS號 | 626-61-9 ![]() |
SMILES |
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性質 | |
化學式 | C5H4ClN |
莫耳質量 | 113.54 g·mol⁻¹ |
外觀 | 無色液體 |
氣味 | 吡啶味 |
密度 | 1.20±0.06 g·cm−3[1] |
熔點 | −43.5 °C(229.7 K)[2] |
沸點 | 147—148 °C(420—421 K)[3] |
相關物質 | |
其他陰離子 | 4-氟吡啶、4-溴吡啶 4-碘吡啶 |
其他陽離子 | 氯苯 |
相關化學品 | 吡啶 |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
4-氯吡啶是一種有機化合物,化學式為C5H4ClN,它是氯吡啶的同分異構體之一。
製備
[編輯]4-氯吡啶可由吡啶-N-氧化物和氯化亞碸反應得到。[4]4-吡啶酮和五硫化二磷反應,得到4-巰基吡啶,再與氯氣反應,得到4-氯吡啶。[5]
4-氯吡啶-N-氧化物在二氯二氧化鉬的催化下由氫氣還原[6],或者直接用LiCl/NaBH4還原[7],都可以得到4-氯吡啶。
反應
[編輯]4-氯吡啶可以在甲醇鉀的存在下(二(亞苄基丙酮)鈀催化)脫氯,得到吡啶。[8]4-氯吡啶的氯也能被其它基團取代,如它和疊氮化鈉反應可以得到4-疊氮基吡啶。[9]它和二氟化銀反應,進一步被鹵代,生成2-氟-4-氯吡啶。[10]
4-氯吡啶可以發生烏爾曼反應,生成4,4'-聯吡啶。[11]在碳酸鉀存在下,它和吡啶-3-硼酸發生鈴木偶聯反應,生成3,4'-聯吡啶。[12]
參考文獻
[編輯]- ^ Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-07-19].
- ^ "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2020-07-19].
- ^ Kamienski, B.; Paluch, M. Influence of halogen isomers of pyridine on the electric surface potential and surface tension in aqueous solutions. Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1965. 13 (9): 643-648. ISSN: 0001-4095.
- ^ Bobrański, Boguslaw; Kochańska, Lidia; Kowalewska, Anna. Über die Einwirkung von Sulfurylchlorid auf Pyridinoxyd. Berichte der deutschen chemischen Gesellschaft (A and B Series). 1938, 71 (11): 2385–2388. ISSN 0365-9488. doi:10.1002/cber.19380711126.
- ^ King, Harold; Ware, Lancelot L. 186. 4–Thiopyridone and derived substances. J. Chem. Soc. 1939, 0 (0): 873–877. ISSN 0368-1769. doi:10.1039/JR9390000873.
- ^ Reis, Patrícia M.; Royo, Beatriz. Chemoselective hydrogenation of nitroarenes and deoxygenation of pyridine N-oxides with H2 catalyzed by MoO2Cl2. Tetrahedron Letters. 2009, 50 (8): 949–952. ISSN 0040-4039. doi:10.1016/j.tetlet.2008.12.038.
- ^ Ram, S. Raja; Chary, K. Purushothama; Iyengar, D. S. An Efficient and Chemoselective Deoxygenation of Hetero Cyclic N-Oxides Using Licl/nabh4. Synthetic Communications. 2000, 30 (19): 3511–3515. ISSN 0039-7911. doi:10.1080/00397910008087263.
- ^ Viciu, Mihai S.; Grasa, Gabriela A.; Nolan, Steven P. Catalytic Dehalogenation of Aryl Halides Mediated by a Palladium/Imidazolium Salt System. Organometallics. 2001, 20 (16): 3607–3612. ISSN 0276-7333. doi:10.1021/om010332s.
- ^ Livi, O.; Ferrarini, P. L.; Tonetti, I.; Smaldone, F.; Zefola, G. Synthesis and pharmacological screening of 1,2,3-triazole derivatives of naphthalene, quinoline, pyridine. Farmaco, Edizione Scientifica, 1979. 34 (3): 217-218. ISSN: 0430-0920.
- ^ Fier, P. S.; Hartwig, J. F. Selective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction. Science. 2013, 342 (6161): 956–960. ISSN 0036-8075. doi:10.1126/science.1243759.
- ^ Puthiaraj, Pillaiyar; Ahn, Wha-Seung. Ullmann coupling of aryl chlorides in water catalyzed by palladium nanoparticles supported on amine-grafted porous aromatic polymer. Molecular Catalysis. 2017, 437: 73–79. ISSN 2468-8231. doi:10.1016/j.mcat.2017.05.003.
- ^ Fleckenstein, Christoph A.; Plenio, Herbert. Highly Efficient Suzuki–Miyaura Coupling of Heterocyclic Substrates through Rational Reaction Design. Chemistry - A European Journal. 2008, 14 (14): 4267–4279. ISSN 0947-6539. doi:10.1002/chem.200701877.