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烟酰氯

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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  checkY
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)[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

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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

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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]N,N'-二烟酰肼[11]

在三氯化铝的存在下,烟酰氯也能和反应,生成3-苯甲酰基吡啶。[5]

参考文献

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  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. ^ 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. ^ 5.0 5.1 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.