四乙基氯化铵

四乙基氯化铵
	IUPAC名; N,N,N-Triethylethanaminium chloride
别名	氯化四乙基铵
识别
CAS号	56-34-8
PubChem	5946
ChemSpider	5733
SMILES	[Cl-].CC[N+](CC)(CC)CC;
InChI	1/C8H20N.ClH/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1;
InChIKey	YMBCJWGVCUEGHA-REWHXWOFAF
ChEBI	78161
性质
化学式	C8H20ClN
摩尔质量	165.7 g·mol−1
外观	无色潮解固体
密度	1.08 g/cm3
熔点	360 °C（633 K）（四水）
溶解性（水）	极易溶
危险性
	致死量或浓度：
LD50（中位剂量）	65 mg/kg（小鼠，腹膜注射）; 900 mg/kg（小鼠，口服）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

四乙基氯化铵，简称TEAC，是一种季铵盐，化学式 (C₂H₅)₄N⁺Cl⁻，有时写作Et₄N⁺Cl⁻。它是吸湿性的无色晶体。在药理学和生理学研究中，它已被用作四乙基铵阳离子的来源，也用于有机化学合成。

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制备和结构

TEAC可以由三乙胺和氯乙烷反应而成。^[2]

TEAC有两种稳定的水合物，分别是一水合物和四水合物。^[3]一水合物TEAC.H₂O 的晶体结构已确定，^[4] 四水合物TEAC.4H₂O也是如此。^[5]

Harmon和Gabriele提供了制备大量TEAC.H2O晶体的详细信息，他们对该化合物和相关化合物进行了红外光谱学研究。^[6]研究人员也指出，尽管刚提纯的 TEAC.H₂O 不含三乙胺盐酸盐，但加热TEAC时会通过霍夫曼消除反应产生少量的三乙胺盐酸盐。

Cl⁻ + H-CH₂-CH₂-N⁺Et₃ → Cl-H + H₂C=CH₂ + Et₃N

合成应用

在很大程度上，TEAC的合成应用类似于四乙基溴化铵(TEAB)和四乙基碘化铵(TEAI)，尽管其中一种盐在特定反应中可能比另一种更有效。举个例子，TEAC在从芳胺、硝基芳烃和一氧化碳制备二芳基脲的反应中作为助催化剂的产率比TEAB和TEAI高。^[7]

在其他示例中，例如以下示例，TEAC不如TEAB或TEAI有效：

通过羧酸的碳酸乙烯酯和某些带有酸性N-H的杂环化合物进行2-羟乙基化（-CH₂-CH₂-OH基团的连接）。^[8]
相转移催化剂在芴的偕二烷基化中，以及氢氧化钠和卤代烷烃水溶液进行苯胺的N,N-二烷基化和咔唑的N-烷基化。^[9]

生物学

与四乙基溴化铵和四乙基碘化铵一样，TEAC已被用作许多临床和药理学研究的四乙基铵离子来源，在四乙基铵盐条目下有更详细的介绍。简而言之，TEAC的神经节阻滞特性已在临床上进行了探索。^[10]虽然它现在作为药物基本上已经过时，但它仍然用于生理研究，因为它能够阻断各种组织中的 K⁺ 通道。^[11]^[12]

毒性

TEAC的毒性是由四乙基铵阳离子导致的，这已被广泛研究。TEAC的急性毒性可以和四乙基溴化铵和四乙基碘化铵比较。这些数据^[13]是用于比较目的，详细信息可在四乙基铵盐条目中找到。

参见

参考资料

[1]
The Merck Index, 10th Ed., p.1316, Rahway: Merck & Co.
[2]
Roose, Peter; Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut, Amines, Aliphatic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a02_001.pub2
[3]
K. M. Harmon, J. M. Gabriele and J. Harmon (1990). "Hydrogen bonding Part 30. New IR spectra-structure correlations for tetraethylammonium, tetramethylammonium, and N,N-dimethyl-pyrrolidinium fluoride monohydrates, tetraethylammonium chloride monohydrate, and tetramethylammonium hydroxide dihydrate; evidence for a planar (H₂O.F⁻)₂ cluster". J. Mol. Struct. 216 53-62.
[4]
J. H. Loehlin and A. Kvick (1978). "Tetraethylammonium chloride monohydrate". Acta Crystallographica Section B 34 3488–3490.
[5]
Y.-S. Lam and T. C. W. Mak (1978). "Crystal data for some tetraethylammonium salt hydrates". 11 193.
[6]
Harmon, Kenneth M.; Gabriele, Julie M. Hydrogen bonding. 11. Infrared study of the water-chloride ion cluster in tetraethylammonium chloride hydrate. Inorganic Chemistry. 1981, 20 (11): 4013–4015. doi:10.1021/ic50225a087.
[7]
H. A. Dieck, R. M. Laine and R. F. Heck (1975). "Low-pressure, palladium-catalyzed N,N'-diarylurea synthesis from nitro compounds, amines, and carbon monoxide". J. Org. Chem. 40 2819–2822.
[8]
T.Yoshino et al. (1977). "Synthetic studies with carbonates. Part 6. Syntheses of 2-hydroxyethyl derivatives by reactions of ethylene carbonate with carboxylic acids or heterocycles in the presence of tetraethylammonium halides or under autocatalytic conditions". J. Chem. Soc., Perkin 1 1266–1272.
[9]
G. Saikia and P. K. Iyer (2010). "Facile C-H alkylation in water: enabling defect-free materials for optoelectronic devices". J. Org. Chem. 75 2714–2717.
[10]
G. K. Moe and W. A. Freyburger (1950). "Ganglionic blocking agents". Pharmacol. Rev. 2 61–95.
[11]
B. Hille (1967). "The selective inhibition of delayed potassium currents in nerve by tetraethylammonium ions". J. Gen. Physiol. 50 1287–1302.
[12]
C. M. Armstrong and B. Hille (1972). "The inner quaternary ammonium receptor in potassium channels of the node of Ranvier". J. Gen. Physiol. 59 388–400.
[13]
O. M. Gruhzit, R. A. Fisken and B. J. Cooper (1948). "Tetraethylammonium chloride [(C₂H₅)₄NCl]. Acute and chronic toxicity in experimental animals". J. Pharmacol. Exp. Ther. 92 103–107.

[Merck-1] [1]
The Merck Index, 10th Ed., p.1316, Rahway: Merck & Co.

[2] [2]
Roose, Peter; Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut, Amines, Aliphatic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a02_001.pub2

[3] [3]
K. M. Harmon, J. M. Gabriele and J. Harmon (1990). "Hydrogen bonding Part 30. New IR spectra-structure correlations for tetraethylammonium, tetramethylammonium, and N,N-dimethyl-pyrrolidinium fluoride monohydrates, tetraethylammonium chloride monohydrate, and tetramethylammonium hydroxide dihydrate; evidence for a planar (H₂O.F⁻)₂ cluster". J. Mol. Struct. 216 53-62.

[4] [4]
J. H. Loehlin and A. Kvick (1978). "Tetraethylammonium chloride monohydrate". Acta Crystallographica Section B 34 3488–3490.

[5] [5]
Y.-S. Lam and T. C. W. Mak (1978). "Crystal data for some tetraethylammonium salt hydrates". 11 193.

[6] [6]
Harmon, Kenneth M.; Gabriele, Julie M. Hydrogen bonding. 11. Infrared study of the water-chloride ion cluster in tetraethylammonium chloride hydrate. Inorganic Chemistry. 1981, 20 (11): 4013–4015. doi:10.1021/ic50225a087.

[7] [7]
H. A. Dieck, R. M. Laine and R. F. Heck (1975). "Low-pressure, palladium-catalyzed N,N'-diarylurea synthesis from nitro compounds, amines, and carbon monoxide". J. Org. Chem. 40 2819–2822.

[8] [8]
T.Yoshino et al. (1977). "Synthetic studies with carbonates. Part 6. Syntheses of 2-hydroxyethyl derivatives by reactions of ethylene carbonate with carboxylic acids or heterocycles in the presence of tetraethylammonium halides or under autocatalytic conditions". J. Chem. Soc., Perkin 1 1266–1272.

[9] [9]
G. Saikia and P. K. Iyer (2010). "Facile C-H alkylation in water: enabling defect-free materials for optoelectronic devices". J. Org. Chem. 75 2714–2717.

[10] [10]
G. K. Moe and W. A. Freyburger (1950). "Ganglionic blocking agents". Pharmacol. Rev. 2 61–95.

[11] [11]
B. Hille (1967). "The selective inhibition of delayed potassium currents in nerve by tetraethylammonium ions". J. Gen. Physiol. 50 1287–1302.

[12] [12]
C. M. Armstrong and B. Hille (1972). "The inner quaternary ammonium receptor in potassium channels of the node of Ranvier". J. Gen. Physiol. 59 388–400.

[13] [13]
O. M. Gruhzit, R. A. Fisken and B. J. Cooper (1948). "Tetraethylammonium chloride [(C₂H₅)₄NCl]. Acute and chronic toxicity in experimental animals". J. Pharmacol. Exp. Ther. 92 103–107.

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