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 |
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| 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）[1] |
| 熔点 | 15—16 °C（288—289 K）[2] |
| 沸点 | 110—113 °C（383—386 K）（25-26 Torr）[3] |
| 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。
合成
[编辑]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
[编辑]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
[编辑]- ^ Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-08-24].
- ^ Hukusima, Yosiro. Tobacco constituents. II. Derivatives of nicotinic acid. Nippon Kagaku Kaishi (1921-47), 1940. 61. 121-124. ISSN: 0369-4208.
- ^ 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.
- ^ 4.0 4.1 4.2 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.
- ^ 5.0 5.1 3-benzoylpyridine. Organic Syntheses. 1957, 37: 6. ISSN 0078-6209. doi:10.15227/orgsyn.037.0006.
- ^ 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.
- ^ 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.
- ^ 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
- ^ 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.
- ^ 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.
- ^ 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.