四乙基氰化铵

四乙基氰化铵是一种季铵盐，化学式为[N(C₂H₅)₄]CN。它可由四乙基溴化铵在无水甲醇中用离子交换树脂处理得到，^[1]或通过四乙基氟硼酸铵和氰化钾反应制得。^[2]它可用于有机合成^[3][4]或制备金属氰配合物。^[5][6]

四乙基氰化铵
别名	氰化四乙基铵
识别
CAS号	13435-20-6  Y
PubChem	3014735
ChemSpider	2283045
SMILES	CC[N+](CC)(CC)CC.[C-]#N
性质
化学式	C9H20N2
摩尔质量	156.27 g·mol−1
外观	白色固体
熔点	254 °C（527 K）
危险性
GHS危险性符号
GHS提示词	危险
H-术语	H300, H310, H330, H400, H410
P-术语	P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P304+340, P310, P320, P321
相关物质
其他阴离子	四乙基氯化铵
其他阳离子	氰化铵
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

参考文献

1. Solodar, John. Tetraalkylammonium cyanides. Synthesis in Inorganic and Metal-Organic Chemistry, 1971. 1 (2): 141-143. ISSN: 0039-789X.
2. Kobler, Heinz; Munz, Rudolf; Al Gasser, Gasser; Simchen, Gerhard. A simple synthesis of tetraalkylammonium salts with functional anions. Justus Liebigs Annalen der Chemie, 1978. 12: 1937. ISSN: 0075-4617.
3. Simchen, G.; Kobler, H. Synthesis of nitriles with tetraalkylammonium cyanides. Synthesis, 1975. 9: 605-607. ISSN: 0039-7881.
4. White, Donald A. Cyanocarboxylation of activated olefins. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1976. 18: 1926-1930. ISSN: 0300-922X.
5. Stephen M. Contakes, Thomas B. Rauchfuss. Alkali metal-templated assembly of the tetrahedral cyanometallate cages [M⊂Mo4(μ-CN)6(CO)12]5− (M = Li, Na). Chemical Communications. 2001, (6): 553–554 [2021-08-02]. doi:10.1039/b010192n.
6. Yuanzhu Zhang, Uma P. Malik, Benjamin Quiggins, Hung Nguyen, Christopher C. Beedle, Alexey E. Kovalev, Rodolphe Clérac, Stephen Hill, Benjamin J. Bythell, Stephen M. Holmes. Structure‐Property Relationships in Tricyanoferrate(III) Building Blocks and Trinuclear Cyanide‐Bridged Complexes. European Journal of Inorganic Chemistry. 2016-06, 2016 (15-16): 2432–2442 [2021-08-02]. ISSN 1434-1948. doi:10.1002/ejic.201600199 （英语）.