4-氯吡啶
化合物
4-氯吡啶是一种有机化合物,化学式为C5H4ClN,它是氯吡啶的同分异构体之一。
4-氯吡啶 | |
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英文名 | 4-chloropyridine |
别名 | 对氯吡啶 p-氯吡啶 |
识别 | |
CAS号 | 626-61-9 |
SMILES |
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性质 | |
化学式 | C5H4ClN |
摩尔质量 | 113.54 g·mol⁻¹ |
外观 | 无色液体 |
气味 | 吡啶味 |
密度 | 1.20±0.06 g·cm−3[1] |
熔点 | −43.5 °C(229.7 K)[2] |
沸点 | 147—148 °C(420—421 K)[3] |
相关物质 | |
其他阴离子 | 4-氟吡啶、4-溴吡啶 4-碘吡啶 |
其他阳离子 | 氯苯 |
相关化学品 | 吡啶 |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
制备
编辑4-氯吡啶可由吡啶-N-氧化物和氯化亚砜反应得到。[4]4-吡啶酮和五硫化二磷反应,得到4-巯基吡啶,再与氯气反应,得到4-氯吡啶。[5]
4-氯吡啶-N-氧化物在二氯二氧化钼的催化下由氢气还原[6],或者直接用LiCl/NaBH4还原[7],都可以得到4-氯吡啶。
反应
编辑4-氯吡啶可以在甲醇钾的存在下(二(亚苄基丙酮)钯催化)脱氯,得到吡啶。[8]4-氯吡啶的氯也能被其它基团取代,如它和叠氮化钠反应可以得到4-叠氮基吡啶。[9]它和二氟化银反应,进一步被卤代,生成2-氟-4-氯吡啶。[10]
4-氯吡啶可以发生乌尔曼反应,生成4,4'-联吡啶。[11]在碳酸钾存在下,它和吡啶-3-硼酸发生铃木偶联反应,生成3,4'-联吡啶。[12]
参考文献
编辑- ^ 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.