烟酰氯

烟酰氯
英文名	nicotinoyl chloride
别名	3-吡啶甲酰氯; 吡啶-3-甲酰氯
识别
CAS号	10400-19-8
SMILES	c1ccncc1C(=O)Cl;
性质
化学式	C6H4ClNO
摩尔质量	141.56 g·mol−1
外观	油状液体
密度	1.297±0.06 g·cm−3（20 °C）
熔点	15—16 °C（288—289 K）
沸点	110—113 °C（383—386 K）（25-26 Torr）
溶解性（水）	水解
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

烟酰氯，也称3-吡啶甲酰氯，是一种有机化合物，化学式为C₆H₄ClNO。

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合成

烟酰氯可由烟酸钾和草酰氯在无水苯中反应得到。^[4]氯化亚砜也可用作酰氯化试剂进行反应，^[5]其它可用溶剂有四氯化碳^[6]、二氯甲烷^[7]等，N,N-二甲基甲酰胺可用作反应的催化剂^[8]。

性质

烟酰氯在潮湿空气中水解，生成烟酰氯盐酸盐。^[4]它和醇反应生成酯，如和无水乙醇反应，生成烟酸乙酯^[4]；和胺反应生成酰胺，如和4-甲基苯胺在二氯甲烷中反应，生成(4-甲基苯基)-3-烟酰胺。^[9]它和肼反应，可以生成烟酰肼^[10]或N,N'-二烟酰肼^[11]。

在三氯化铝的存在下，烟酰氯也能和苯反应，生成3-苯甲酰基吡啶。^[5]

参考文献

[1]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-08-24].
[2]
Hukusima, Yosiro. Tobacco constituents. II. Derivatives of nicotinic acid. Nippon Kagaku Kaishi (1921-47), 1940. 61. 121-124. ISSN: 0369-4208.
[3]
Chiang, Ming-Chien; Hartung, Walter H. SYNTHESIS OF DIALKYLAMINOAKLYL ESTERS OF PYRIDINE-CARBOXYLIC ACIDS. The Journal of Organic Chemistry. 1945, 10 (1): 26–28. ISSN 0022-3263. doi:10.1021/jo01177a005.
[4]
Wingfield, H. N.; Harlan, W. R.; Hanmer, H. R. The Preparation of Nicotinyl Chloride. Journal of the American Chemical Society. 1953, 75 (17): 4364–4364. ISSN 0002-7863. doi:10.1021/ja01113a530.
[5]
3-benzoylpyridine. Organic Syntheses. 1957, 37: 6. ISSN 0078-6209. doi:10.15227/orgsyn.037.0006.
[6]
Zinner, Helmut; Fiedler, Heinz. Nicotinic acid phenol esters with antimycotic and hyperemic-like activity. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1958. 291/63. 330-338. ISSN: 0376-0367.
[7]
Chen, Yang; Liu, Yu; Zhang, Xiao; Lu, Da; Yang, Lixin; Deng, Junfeng; Deng, Shengqi. Copper Catalyzed Direct Synthesis of Nitriles from Acyl Azides. ChemistrySelect. 2018, 3 (43): 12325–12329. ISSN 2365-6549. doi:10.1002/slct.201802918.
[8]
Priya, B. S., Basappa, Nanjunda Swamy, S., & Rangappa, K. S. (2005). Synthesis and characterization of novel 6-fluoro-4-piperidinyl-1,2-benzisoxazole amides and 6-fluoro-chroman-2-carboxamides: antimicrobial studies. Bioorganic & Medicinal Chemistry, 13(7), 2623–2628. doi:10.1016/j.bmc.2005.01.026
[9]
Mocilac, Pavle; Gallagher, John F. Structural systematics and conformational analyses of a 3 × 3 isomer grid of nine N-(tolyl)pyridinecarboxamides and three chlorinated relatives. CrystEngComm. 2011, 13 (17): 5354. ISSN 1466-8033. doi:10.1039/c1ce05169e.
[10]
Ramalakshmi, N.; Aruloly, L.; Arunkumar, S.; Ilango, K.; Puratchikody, A. Synthesis and Biological Evaluation of Some Novel Nicotinic Acid Derivatives. Malaysian Journal of Science. 2009, 28 (2): 197–203. ISSN 1394-3065. doi:10.22452/mjs.vol28no2.8.
[11]
Pamar, Malavath Geeta; Gannimani, Ramesh; Govender, Patrick; Ramjugernath, Deresh; Nanjundaswamy, Hemmaragala Marishetty. Rapid generation of N,N'-diacylhydrazines by I2 or Br2/hydrazine hydrate: a facile route to 1,3,4-oxadiazoles. Organic Chemistry: An Indian Journal, 2014. 10 (1): 17-23. ISSN: 0974-7516.

[1] [1]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-08-24].

[2] [2]
Hukusima, Yosiro. Tobacco constituents. II. Derivatives of nicotinic acid. Nippon Kagaku Kaishi (1921-47), 1940. 61. 121-124. ISSN: 0369-4208.

[3] [3]
Chiang, Ming-Chien; Hartung, Walter H. SYNTHESIS OF DIALKYLAMINOAKLYL ESTERS OF PYRIDINE-CARBOXYLIC ACIDS. The Journal of Organic Chemistry. 1945, 10 (1): 26–28. ISSN 0022-3263. doi:10.1021/jo01177a005.

[Wingfield-4] [4]
Wingfield, H. N.; Harlan, W. R.; Hanmer, H. R. The Preparation of Nicotinyl Chloride. Journal of the American Chemical Society. 1953, 75 (17): 4364–4364. ISSN 0002-7863. doi:10.1021/ja01113a530.

[orgsyn-5] [5]
3-benzoylpyridine. Organic Syntheses. 1957, 37: 6. ISSN 0078-6209. doi:10.15227/orgsyn.037.0006.

[6] [6]
Zinner, Helmut; Fiedler, Heinz. Nicotinic acid phenol esters with antimycotic and hyperemic-like activity. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1958. 291/63. 330-338. ISSN: 0376-0367.

[7] [7]
Chen, Yang; Liu, Yu; Zhang, Xiao; Lu, Da; Yang, Lixin; Deng, Junfeng; Deng, Shengqi. Copper Catalyzed Direct Synthesis of Nitriles from Acyl Azides. ChemistrySelect. 2018, 3 (43): 12325–12329. ISSN 2365-6549. doi:10.1002/slct.201802918.

[8] [8]
Priya, B. S., Basappa, Nanjunda Swamy, S., & Rangappa, K. S. (2005). Synthesis and characterization of novel 6-fluoro-4-piperidinyl-1,2-benzisoxazole amides and 6-fluoro-chroman-2-carboxamides: antimicrobial studies. Bioorganic & Medicinal Chemistry, 13(7), 2623–2628. doi:10.1016/j.bmc.2005.01.026

[9] [9]
Mocilac, Pavle; Gallagher, John F. Structural systematics and conformational analyses of a 3 × 3 isomer grid of nine N-(tolyl)pyridinecarboxamides and three chlorinated relatives. CrystEngComm. 2011, 13 (17): 5354. ISSN 1466-8033. doi:10.1039/c1ce05169e.

[10] [10]
Ramalakshmi, N.; Aruloly, L.; Arunkumar, S.; Ilango, K.; Puratchikody, A. Synthesis and Biological Evaluation of Some Novel Nicotinic Acid Derivatives. Malaysian Journal of Science. 2009, 28 (2): 197–203. ISSN 1394-3065. doi:10.22452/mjs.vol28no2.8.

[11] [11]
Pamar, Malavath Geeta; Gannimani, Ramesh; Govender, Patrick; Ramjugernath, Deresh; Nanjundaswamy, Hemmaragala Marishetty. Rapid generation of N,N'-diacylhydrazines by I2 or Br2/hydrazine hydrate: a facile route to 1,3,4-oxadiazoles. Organic Chemistry: An Indian Journal, 2014. 10 (1): 17-23. ISSN: 0974-7516.

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