4-氯吡啶

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	n1ccc(Cl)cc1;
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
熔点	−43.5 °C（229.7 K）
沸点	147—148 °C（420—421 K）
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。

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。

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制备

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

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

[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.

[1] [1]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-07-19].

[2] [2]
"PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2020-07-19].

[3] [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] [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] [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] [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] [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] [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] [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] [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] [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] [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.

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