四甲基碘化铵

四甲基碘化铵
英文名	Tetramethylammonium iodide
别名	碘化四甲基铵; 碘化四甲铵
识别
CAS号	75-58-1
SMILES	C[N+](C)(C)C.[I-];
EINECS	200-881-3
性质
化学式	C4H12IN
摩尔质量	201.05 g·mol−1
外观	无色晶体
密度	1.829 g·cm−3
熔点	≥241 °C（分解）; >360 °C（分解）
溶解性（水）	微溶于水，难溶于氯仿和乙醚
危险性
H-术语	H315, H319, H335
P-术语	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P362, P403+233, P501
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

四甲基碘化铵是一种季铵盐，化学式为[(CH₃)₄N]I，为无色晶体。

制备

四甲基碘化铵可由三甲胺和碘甲烷的气相反应生成。^[3]甲醇、碘甲烷和28%氨溶液反应，^[4]或者N,N-二甲基甲酰胺和碘甲烷在25%的碱溶液（氨、氢氧化钠或氢氧化钾）中反应，都可以得到该季铵盐。^[5]

结构

四甲基碘化铵属四方晶系，空间群P4/nmm，晶胞参数a=7.9643 Å, b=5.7550 Å（30 °C）。^[6]

性质及用途

四甲基碘化铵和叠氮化亚铊反应，可以得到四甲基叠氮化铵：^[7]

[(CH₃)₄N]I + TlN₃ → [(CH₃)₄N]N₃ + TlI

它与硫、氰化亚铜反应，可以得到配合物[(CH₃)₄N][Cu(SCN)I]。^[8]它和碘化铅在γ-丁内酯中反应，可以得到具有钙钛矿结构的[(CH₃)₄N][PbI₃]。^[9]

它和路易斯酸共同使用，可用作四羰基钴钠催化的三甲胺羰基化反应的引发剂。^[10]

参考文献

^ Philip N. James, H. R. Snyder. Synthesis and Reactions of α-Cyanogramine 1. Journal of the American Chemical Society. 1960-02, 82 (3): 589–593 [2019-06-14]. ISSN 0002-7863. doi:10.1021/ja01488a022 （英语）.
^ O. E. Zhuravlev, V. M. Nikol’skii, L. I. Voronchikhina. Thermal stability of quaternary ammonium hexafluorophosphates and halides. Russian Journal of Applied Chemistry. 2013-06, 86 (6): 824–830 [2019-06-14]. ISSN 1070-4272. doi:10.1134/S1070427213060062 （英语）.
^ F. A. Petrachkov. Kinetics of formation of a quaternary ammonium salt from gaseous components. Zhurnal Fizicheskoi Khimii, 1954. 28: 1408-1416. ISSN: 0044-4537
^ Esteban Szabo. Formation of tetramethylammonium iodide. Farm. chilena, 1952. 26: 295-297. CAN47: 13862
^ D. Dzharov; Atanas Iovchev. Preparation of tetramethylammonium iodide（德文）. Oesterreichische Chemiker-Zeitung, 1967. 68 (9): 305-306. ISSN: 0369-7061.
^ Alex Xenopoulos, Martina Ralle, Anton Habenschuss, Bernhard Wunderlich. X-ray powder diffraction data and thermal expansion of N(CH 3 ) 4 Br and N(CH 3 ) 4 I. Powder Diffraction. 1996-09, 11 (3): 246–249 [2019-06-14]. ISSN 0885-7156. doi:10.1017/S0885715600009192 （英语）.
^ Kukushkin, I. K.; Velikanova, E. V.; Zlobin, V. A. Methods for preparation of quaternary ammonium azides（俄文）. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya, 2010. 53 (3): 108-110. ISSN: 0579-2991
^ Xi Liu, Kun-Lin Huang, Guo-Ming Liang, Ming-Sheng Wang, Guo-Cong Guo. Molecular design of luminescent halogeno-thiocyano-d10 metal complexes with in situ formation of the thiocyanate ligand. CrystEngComm. 2009, 11 (8): 1615 [2019-06-14]. ISSN 1466-8033. doi:10.1039/b902121c （英语）.
^ Qiu, Yu; Guan, Xiangfeng; Jiang, Linqin; Yan, Fengpo; Yan, Qiong. High-stability hybrid perovskite photoelectric material consisting of organic amine cation, metal cation and halogen anion for solar cell device or electroluminescent device[P]. 2014. CN 104447349 A
^ Yizhu Lei, Rui Zhang, Wenjia Han, Hui Mei, Yanlong Gu, Bo Xiao, Guangxing Li. Promotion effects of Lewis acid/(CH3)4NI on [Co(CO)4]ˉ-catalyzed C–N bond activation in the carbonylation of trimethylamine. Catalysis Communications. 2013-08, 38: 45–49 [2019-06-14]. doi:10.1016/j.catcom.2013.04.017. （原始内容存档于2018-06-30）（英语）.

[1] Philip N. James, H. R. Snyder. Synthesis and Reactions of α-Cyanogramine 1. Journal of the American Chemical Society. 1960-02, 82 (3): 589–593 [2019-06-14]. ISSN 0002-7863. doi:10.1021/ja01488a022 （英语）.

[2] O. E. Zhuravlev, V. M. Nikol’skii, L. I. Voronchikhina. Thermal stability of quaternary ammonium hexafluorophosphates and halides. Russian Journal of Applied Chemistry. 2013-06, 86 (6): 824–830 [2019-06-14]. ISSN 1070-4272. doi:10.1134/S1070427213060062 （英语）.

[3] F. A. Petrachkov. Kinetics of formation of a quaternary ammonium salt from gaseous components. Zhurnal Fizicheskoi Khimii, 1954. 28: 1408-1416. ISSN: 0044-4537

[4] Esteban Szabo. Formation of tetramethylammonium iodide. Farm. chilena, 1952. 26: 295-297. CAN47: 13862

[5] D. Dzharov; Atanas Iovchev. Preparation of tetramethylammonium iodide（德文）. Oesterreichische Chemiker-Zeitung, 1967. 68 (9): 305-306. ISSN: 0369-7061.

[6] Alex Xenopoulos, Martina Ralle, Anton Habenschuss, Bernhard Wunderlich. X-ray powder diffraction data and thermal expansion of N(CH 3 ) 4 Br and N(CH 3 ) 4 I. Powder Diffraction. 1996-09, 11 (3): 246–249 [2019-06-14]. ISSN 0885-7156. doi:10.1017/S0885715600009192 （英语）.

[7] Kukushkin, I. K.; Velikanova, E. V.; Zlobin, V. A. Methods for preparation of quaternary ammonium azides（俄文）. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya, 2010. 53 (3): 108-110. ISSN: 0579-2991

[8] Xi Liu, Kun-Lin Huang, Guo-Ming Liang, Ming-Sheng Wang, Guo-Cong Guo. Molecular design of luminescent halogeno-thiocyano-d10 metal complexes with in situ formation of the thiocyanate ligand. CrystEngComm. 2009, 11 (8): 1615 [2019-06-14]. ISSN 1466-8033. doi:10.1039/b902121c （英语）.

[9] Qiu, Yu; Guan, Xiangfeng; Jiang, Linqin; Yan, Fengpo; Yan, Qiong. High-stability hybrid perovskite photoelectric material consisting of organic amine cation, metal cation and halogen anion for solar cell device or electroluminescent device[P]. 2014. CN 104447349 A

[10] Yizhu Lei, Rui Zhang, Wenjia Han, Hui Mei, Yanlong Gu, Bo Xiao, Guangxing Li. Promotion effects of Lewis acid/(CH3)4NI on [Co(CO)4]ˉ-catalyzed C–N bond activation in the carbonylation of trimethylamine. Catalysis Communications. 2013-08, 38: 45–49 [2019-06-14]. doi:10.1016/j.catcom.2013.04.017. （原始内容存档于2018-06-30）（英语）.

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