4-氯吡啶

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4-氯吡啶
英文名 4-chloropyridine
别名 对氯吡啶
p-氯吡啶
识别
CAS号 626-61-9  ✓
SMILES
性质
化学式 C5H4ClN
摩尔质量 113.54 g·mol⁻¹
外观 无色液体
氣味 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,所有数据均出自一般条件(25 ℃,100 kPa)下。

4-氯吡啶是一种有机化合物,化学式为C5H4ClN,它是氯吡啶同分异构体之一。

制备[编辑]

4-氯吡啶可由吡啶-N-氧化物氯化亚砜反应得到。[4]4-吡啶酮德语4-Pyridon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]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]

3-pyridineboronic acid + 4-chloropyridine.png

参考文献[编辑]

  1. ^ Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-07-19].
  2. ^ "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2020-07-19].
  3. ^ 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.
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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.
  10. ^ 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. 
  11. ^ 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. 
  12. ^ 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.