煙酰氯

煙酰氯
英文名	nicotinoyl chloride
別名	3-吡啶甲酰氯; 吡啶-3-甲酰氯
識別
CAS號	10400-19-8
SMILES	c1ccncc1C(=O)Cl;
性質
化學式	C6H4ClNO
摩爾質量	141.56 g·mol−1
外觀	油狀液體
密度	1.297±0.06 g·cm−3（20 °C）
熔點	15—16 °C（288—289 K）
沸點	110—113 °C（383—386 K）（25-26 Torr）
溶解性（水）	水解
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

煙酰氯，也稱3-吡啶甲酰氯，是一種有機化合物，化學式為C₆H₄ClNO。

合成

煙酰氯可由煙酸鉀和草酰氯在無水苯中反應得到。^[4]氯化亞碸也可用作酰氯化試劑進行反應，^[5]其它可用溶劑有四氯化碳^[6]、二氯甲烷^[7]等，N,N-二甲基甲酰胺可用作反應的催化劑^[8]。

性質

煙酰氯在潮濕空氣中水解，生成煙酰氯鹽酸鹽。^[4]它和醇反應生成酯，如和無水乙醇反應，生成煙酸乙酯^[4]；和胺反應生成酰胺，如和4-甲基苯胺在二氯甲烷中反應，生成(4-甲基苯基)-3-煙酰胺。^[9]它和肼反應，可以生成煙酰肼^[10]或N,N'-二煙酰肼^[11]。

在三氯化鋁的存在下，煙酰氯也能和苯反應，生成3-苯甲酰基吡啶。^[5]

參考文獻

^ 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.

[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.

[Wingfield-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.

[orgsyn-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.

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