4-氯吡啶

4-氯吡啶
英文名	4-chloropyridine
別名	對氯吡啶; p-氯吡啶
識別
CAS號	626-61-9
SMILES	n1ccc(Cl)cc1;
性質
化學式	C5H4ClN
摩爾質量	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
熔點	−43.5 °C（229.7 K）
沸點	147—148 °C（420—421 K）
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

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

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

^ 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.

[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.

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