1-(氰基甲基)-3-甲基-1H-咪唑-3-鎓氯化物 | 154312-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(氰基甲基)-3-甲基-1H-咪唑-3-鎓氯化物
• 中文别名: 1-甲基-3-(氰甲基)氯化咪唑；1-(氰甲基)-3-甲基氯化咪唑
• 英文名称: 1-(cyanomethyl)-3-methylimidazolium chloride
• 英文别名: 3-(cyanomethyl)-1-methylimidazolium chloride；3-cyanomethyl-1-methylimidazolinium chloride；1-cyanomethyl-3-methylimidazolium chloride；1-methyl-3-cyanomethylimidazolium chloride；3-cyanomethyl-1-methylimidazolium chloride；[AMim]Cl；2-(3-methylimidazol-3-ium-1-yl)acetonitrile;chloride
• CAS: 154312-63-7
• 化学式: C₆H₈N₃*Cl
• 分子量: 157.603
• InChiKey: WBDDQUDDZPKVRV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.16
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R37/38

反应信息

• 作为反应物：
  描述：

  1-(氰基甲基)-3-甲基-1H-咪唑-3-鎓氯化物 在 sodium azide 、 zinc dibromide 、 盐酸 作用下， 以 水 为溶剂， 生成 1-(5-1H-tetrazolyl)methyl-3-methylimidazolium chloride
  参考文献：
  名称：

  A general design platform for ionic liquid ions based on bridged multi-heterocycles with flexible symmetry and charge

  摘要：

  开发了一种概念设计平台，用于制备具有可变杂环、桥联、对称性和电荷的新型离子液体，通过简单的烷基化、点击反应和离子液体化学方法实现，并以1-(2-(5-四唑基)乙基)-3-(5-1H-四唑基)甲基咪唑盐及其转化为室温离子液体作为阳离子或阴离子进行了验证。

  DOI：

  10.1039/c002861d
• 作为产物：
  描述：

  N-甲基咪唑 、 氯乙腈 以90%的产率得到1-(氰基甲基)-3-甲基-1H-咪唑-3-鎓氯化物
  参考文献：
  名称：

  A general design platform for ionic liquid ions based on bridged multi-heterocycles with flexible symmetry and charge

  摘要：

  开发了一种概念设计平台，用于制备具有可变杂环、桥联、对称性和电荷的新型离子液体，通过简单的烷基化、点击反应和离子液体化学方法实现，并以1-(2-(5-四唑基)乙基)-3-(5-1H-四唑基)甲基咪唑盐及其转化为室温离子液体作为阳离子或阴离子进行了验证。

  DOI：

  10.1039/c002861d

文献信息

• General Reductive Amination of Aldehydes and Ketones with Amines and Nitroaromatics under H₂ by Recyclable Iridium Catalysts
  作者：Dejun Sui、Fei Mao、Haipeng Fan、Zhengliang Qi、Jun Huang

  DOI：10.1002/cjoc.201600903

  日期：2017.9

  applied for the reductive amination of aldehydes and ketones with nitroaromatics and amines using H2. The iridium catalysts were prepared by pyrolysis of ionic liquid 1‐methyl‐3‐cyanomethylimidazoulium chloride ([MCNI]Cl) with iridium chloride (IrCl3) in activated carbons. Iridium particles were well dispersed and stable in the N‐doped carbon materials from [MCNI]Cl with activated carbon. The Ir@NC(600‐2h)

  制备了多相铱催化剂，并将其用于使用H 2与硝基芳族化合物和胺进行醛和酮的还原胺化反应。通过在活性炭中将离子液体1-甲基-3-氰基甲基咪唑氯化铝（[MCNI] Cl）与氯化铱（IrCl 3）热解制备铱催化剂。铱颗粒在[MCNI] Cl含活性炭的N掺杂碳材料中分散良好且稳定。发现Ir @ NC（600-2h）催化剂具有高活性，并且对于使用H 2还原醛和酮的胺化反应具有选择性然后将各种硝基苯和胺选择性地转化为相应的仲胺和叔胺。Ir @ NC（600-2h）催化剂可以重复使用多次，而不会明显失活。
• [EN] IONIC LIQUIDS BASED ON IMIDAZOLIUM SALTS INCORPORATING A NITRILE FUNCTIONALITY<br/>[FR] LIQUIDES IONIQUES A BASE DE SELS D'IMIDAZOLIUM INCORPORANT UNE FONCTIONNALITE NITRILE
  申请人：ECOLE POLYTECH

  公开号：WO2005019185A1

  公开（公告）日：2005-03-03

  Novel chemical compounds of the general formula K+A-, in which K+ is a 5- or 6- membered heterocyclic ring having 1-3 hetereo atoms, which can be independently N, S, or 0; with the proviso that at least one of the hetereo atoms must be a quaternized nitrogen atom having a -R'CN substituent, wherein R' is alkyl (C1 to C12); the heterocyclic ring having up to 4 or 5 substituents independently chosen from the moieties: (i) H; (ii) halogen or (iii) alkyl (C1 to C12) , which is unsubstituted or partially or fully substituted by further groups, preferably F, Cl, N(CnF(2n+1-x)Hx)2, O(CnF(2n+1-x)Hx), S02(CnF(2n+1-x)Hx)2 or CnF(2n+1-x)Hx where 1

  通用公式K+A-的新化合物，其中K+是一个含有1-3个杂原子的5-或6-成员杂环，这些杂原子可以独立地是N、S或O；但其中至少一个杂原子必须是一个具有-R'CN取代基的季铵氮原子，其中R'是烷基（C1到C12）；该杂环最多有4或5个取代基，可以独立选择自以下基团：(i) H；(ii) 卤素或(iii) 烷基（C1到C12），该烷基未取代或部分或完全被进一步的基团取代，优选为F、Cl、N(CnF(2n+1-x)Hx)2、O(CnF(2n+1-x)Hx)、S02(CnF(2n+1-x)Hx)2或CnF(2n+1-x)Hx，其中1
• Synthesis of N-cyanoalkyl-functionalized imidazolium nitrate and dicyanamide ionic liquids with a comparison of their thermal properties for energetic applications
  作者：David M. Drab、Marcin Smiglak、Julia L. Shamshina、Steven P. Kelley、Stefan Schneider、Tommy W. Hawkins、Robin D. Rogers

  DOI：10.1039/c0nj00889c

  日期：——

  The synthesis of 10 N-alkyl-N-cyanoalkyl-functionalized imidazolium (N-methyl- and N-butyl-N-((CH2)nCN)imidazolium; n = 1–4) nitrate and 11 N-alkyl-N-cyanoalkyl-functionalized imidazolium (N-methyl-N-((CH2)nCN)imidazolium; n = 1–6, N-(2-cyanoethyl)-N-((CH2)nCN)imidazolium; n = 1,3–6) dicyanamide salts was achieved via N-alkylation of substituted imidazoles with commercially available haloalkylnitriles followed by anion exchange. Based on their observed melting points, all dicyanamide salts and all but one nitrate salt (1-cyanomethyl-3-methylimidazolium nitrate) had melting points <100 °C, as did 13 of the 17 halide precursors also reported here. Differential scanning calorimetry data indicated that melting points decreased by increasing the N-alkyl or N-cyanoalkyl chain length or by exchanging with the dicyanamide anion, which produced the lowest melting points in comparison to analogous halide or nitrate salts. Thermogravimetric analyses indicated that thermal stability increased for longer N-cyanoalkyl substituent lengths and decreased significantly for nitrates and more so for dicyanamides bearing short-chain N-cyanoalkyl substituents (e.g., N-cyanomethyl, N-(1-cyanoethyl), and N-(2-cyanoethyl)) in comparison to halide precursors. Furthermore, for many of the N-cyanoalkyl-substituted salts (especially the dicyanamides), there was a significant production of thermally-stable char – presumably due to by-products formed from the reaction of either N-cyanoalkyl substituents, dicyanamide anion, or both, which resulted in thermally-stable polymers or cycles.

  通过将市售的卤代烷基腈与取代咪唑进行N-烷基化反应，然后进行阴离子交换，成功合成了10种N-烷基-N-氰基烷基功能化的咪唑鎓（N-甲基-和N-丁基-N-((CH2)nCN)咪唑鎓；n = 1–4）硝酸盐和11种N-烷基-N-氰基烷基功能化的咪唑鎓（N-甲基-N-((CH2)nCN)咪唑鎓；n = 1–6，N-(2-氰乙基)-N-((CH2)nCN)咪唑鎓；n = 1,3–6）二氰胺盐。根据它们的熔点观测结果，所有二氰胺盐和除一种硝酸盐（1-氰甲基-3-甲基咪唑鎓硝酸盐）外的所有硝酸盐的熔点均低于100 °C，这里还报道的17种卤化物前体中也有13种的熔点低于100 °C。差示扫描量热数据表明，熔点随着N-烷基或N-氰基烷基链长的增加或与二氰胺阴离子交换而降低，这使得与类似的卤化物或硝酸盐相比熔点最低。热重分析显示，随着N-氰基烷基取代基长度的增加，热稳定性增加，而对于硝酸盐和特别是短链N-氰基烷基取代基（例如，N-氰甲基，N-(1-氰乙基)和N-(2-氰乙基)）的二氰胺盐，热稳定性显著降低。此外，许多N-氰基烷基取代的盐（尤其是二氰胺盐），存在大量热稳定的炭质产物——这可能是由于N-氰基烷基取代基、二氰胺阴离子或两者的反应产物形成了热稳定的聚合物或环。
• Hypergolic fuels based on water-stable borohydride cluster anions with ultralow ignition delay times
  作者：Nianming Jiao、Yanqiang Zhang、Long Liu、Jean'ne M. Shreeve、Suojiang Zhang

  DOI：10.1039/c7ta04038e

  日期：——

  In bipropulsion systems, hypergolic ionic liquids with B-H groups, as promising alternatives to toxic hydrazine-based fuels, can improve propulsion performance. A series of borohydride cluster-based salts with excellent hydrolytic and thermal stabilities (Td > 200 °С), and the highest density (1.18 g cm-3) of any known borohydride hypergolic ionic liquids were prepared. Upon contact with white fuming

  在双推进系统中，具有BH基团的高离子性离子液体作为有毒肼基燃料的有前途的替代品，可以改善推进性能。制备了一系列基于硼氢化物簇的盐，具有优异的水解和热稳定性（Td> 200°С），并且在任何已知的硼氢化物超高分子量离子液体中具有最高的密度（1.18 g cm-3）。与白色发烟硝酸或N2O4接触后，这些新盐具有超快的点火延迟时间（低至1 ms），具有出色的点火性能。为了了解它们的高稳定性和良好的点火性能，进行了理论研究。
• Domino reaction of N-(cyanomethyl)-1,3-azolium quaternary salts with o-hydroxybenzaldehydes: scope and limitations
  作者：L. G. Voskressensky、A. A. Festa、O. A. Storozhenko、T. A. Le、V. T. Nguyen、A. V. Varlamov

  DOI：10.1039/c4ra14122a

  日期：——

  A route towards chromenes, annulated with an imidazo[5,1-c][1,4]thiazine core through a base-promoted domino reaction of thiazolium quaternary salts, has been developed. The synthesised compounds show high cytotoxic activity against human tumour cell lines.

  已经开发了通过咪唑鎓季盐的碱促进的多米诺反应，与咪唑并[5,1- c ] [1,4]噻嗪核成环的色烯的途径。合成的化合物显示出对人肿瘤细胞系的高细胞毒性活性。