四甲基碘化銨

四甲基碘化銨
英文名	Tetramethylammonium iodide
別名	碘化四甲基銨; 碘化四甲銨
識別
CAS號	75-58-1
SMILES	C[N+](C)(C)C.[I-];
EINECS	200-881-3
性質
化學式	C4H12IN
摩爾質量	201.05 g·mol−1
外觀	無色晶體
密度	1.829 g·cm−3
熔點	≥241 °C（分解）; >360 °C（分解）
溶解性（水）	微溶於水，難溶於氯仿和乙醚
危險性
H-術語	H315, H319, H335
P-術語	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P362, P403+233, P501
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

四甲基碘化銨是一種季銨鹽，化學式為[(CH₃)₄N]I，為無色晶體。

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製備

四甲基碘化銨可由三甲胺和碘甲烷的氣相反應生成。^[3]甲醇、碘甲烷和28%氨溶液反應，^[4]或者N,N-二甲基甲酰胺和碘甲烷在25%的鹼溶液（氨、氫氧化鈉或氫氧化鉀）中反應，都可以得到該季銨鹽。^[5]

結構

四甲基碘化銨屬四方晶系，空間群P4/nmm，晶胞參數a=7.9643 Å, b=5.7550 Å（30 °C）。^[6]

性質及用途

四甲基碘化銨和疊氮化亞鉈反應，可以得到四甲基疊氮化銨：^[7]

[(CH₃)₄N]I + TlN₃ → [(CH₃)₄N]N₃ + TlI

它與硫、氰化亞銅反應，可以得到配合物[(CH₃)₄N][Cu(SCN)I]。^[8]它和碘化鉛在γ-丁內酯中反應，可以得到具有鈣鈦礦結構的[(CH₃)₄N][PbI₃]。^[9]

它和路易斯酸共同使用，可用作四羰基鈷鈉催化的三甲胺羰基化反應的引發劑。^[10]

參考文獻

[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 （英語）.
[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 （英語）.
[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 （英語）.
[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 （英語）.
[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. （原始內容存檔於2018-06-30）（英語）.

[1] [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 （英語）.

[2] [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 （英語）.

[3] [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] [4]
Esteban Szabo. Formation of tetramethylammonium iodide. Farm. chilena, 1952. 26: 295-297. CAN47: 13862

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

[6] [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 （英語）.

[7] [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] [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 （英語）.

[9] [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] [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. （原始內容存檔於2018-06-30）（英語）.

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