1-(ferrocenylmethyl)-4-methyltriazolium iodide | 713108-32-8

• 英文名称: 1-(ferrocenylmethyl)-4-methyltriazolium iodide
• 英文别名: 1-ferrocenylmethy-4-methyltriazolium iodide
• CAS: 713108-32-8
• 化学式: C₁₄H₁₆FeN₃*I
• 分子量: 409.053
• InChiKey: ZVWGGWXUYKDTKL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1-(ferrocenylmethyl)-4-methyltriazolium iodide 、 bis(trifluoromethane)sulfonimide lithium 以 not given 为溶剂， 以96%的产率得到1-(ferrocenylmethyl)-4-methyltriazolium bis(trifluoromethanesulfonyl)amide
  参考文献：
  名称：

  The First (Ferrocenylmethyl)imidazolium and (Ferrocenylmethyl)triazolium Room Temperature Ionic Liquids

  摘要：

  N-(Ferrocenylmethyl)imidazole (3a), 1-(ferrocenylmethyl)-1,2,4-triazole (3b), 1,1'-bis[(1H-imidazol-1-yl)methyl]ferrocene (8a), 1,1'-bis [(1H-(2-methyl)imidazol-1-yl)methyl]ferrocene (8b), and 1,1'-bis[(1H-1,2,4-triazol-1-yl)methyl]ferrocene (8c) were synthesized in moderate yields. These compounds were quaternized with methyl iodide to form 1-(ferrocenylmethyl)-3-methylimidazolium iodide (4a), 1-(ferrocenylmethyl)-4-methyl-1,2,4-triazolium iodide (4b), 1,1'-bis{[1-(2,3-dimethyl)imidazolium]methyl}ferrocene diiodide (9b), and 1,1'-bis{[1-(4-methyl)-1,2,4-triazolium]methyl}ferrocene diiodide (9c), respectively, in excellent yields. Compounds 4a, 4b, 9b, and 9c were metathesized with bis(trifluoromethanesulfonyl)amide to give high yields of 5a, 5b, 10b, and 10c. With potassium hexafluorophosphate, 9b forms 10d. Salts 5a, 5b, and 10c are the first room-temperature ionic liquids with cations containing an organometallic moiety that exhibit T-g values well below room temperature, i.e., -32, -16, and -11 degreesC. The compounds were characterized by H-1, F-19, and C-13 NMR, MS, and elemental analyses. T-g values and melting points were determined by DSC. T-d values (5% weight loss temperature) were recorded by TGA. X-ray single-crystal structures show that 9c and 10d crystallize in the triclinic space group P (1) over bar.

  DOI：

  10.1021/ic049961v
• 作为产物：
  描述：

  1-ferrocenylmethyl-1H-1,2,4-triazole 、 碘甲烷 以 neat (no solvent) 为溶剂， 以95%的产率得到1-(ferrocenylmethyl)-4-methyltriazolium iodide
  参考文献：
  名称：

  The First (Ferrocenylmethyl)imidazolium and (Ferrocenylmethyl)triazolium Room Temperature Ionic Liquids

  摘要：

  N-(Ferrocenylmethyl)imidazole (3a), 1-(ferrocenylmethyl)-1,2,4-triazole (3b), 1,1'-bis[(1H-imidazol-1-yl)methyl]ferrocene (8a), 1,1'-bis [(1H-(2-methyl)imidazol-1-yl)methyl]ferrocene (8b), and 1,1'-bis[(1H-1,2,4-triazol-1-yl)methyl]ferrocene (8c) were synthesized in moderate yields. These compounds were quaternized with methyl iodide to form 1-(ferrocenylmethyl)-3-methylimidazolium iodide (4a), 1-(ferrocenylmethyl)-4-methyl-1,2,4-triazolium iodide (4b), 1,1'-bis{[1-(2,3-dimethyl)imidazolium]methyl}ferrocene diiodide (9b), and 1,1'-bis{[1-(4-methyl)-1,2,4-triazolium]methyl}ferrocene diiodide (9c), respectively, in excellent yields. Compounds 4a, 4b, 9b, and 9c were metathesized with bis(trifluoromethanesulfonyl)amide to give high yields of 5a, 5b, 10b, and 10c. With potassium hexafluorophosphate, 9b forms 10d. Salts 5a, 5b, and 10c are the first room-temperature ionic liquids with cations containing an organometallic moiety that exhibit T-g values well below room temperature, i.e., -32, -16, and -11 degreesC. The compounds were characterized by H-1, F-19, and C-13 NMR, MS, and elemental analyses. T-g values and melting points were determined by DSC. T-d values (5% weight loss temperature) were recorded by TGA. X-ray single-crystal structures show that 9c and 10d crystallize in the triclinic space group P (1) over bar.

  DOI：

  10.1021/ic049961v

文献信息

• Low-migratory ionic ferrocene-based burning rate catalysts with high combustion catalytic efficiency
  作者：Xuelin Liu、Weiqiang Zhang、Guofang Zhang、Ziwei Gao

  DOI：10.1039/c4nj01216j

  日期：——

  exhibit quasi-reversible redox systems. Migration studies confirmed that the migration of these ionic ferrocenes is much slower than that of 2,2-bis(ethylferrocenyl)propane. The migration trend of the compounds is dependent on molecular structures of the ionic ferrocenes and that shorter alkyl chain lengths in the heterocyclic rings lead to slower migration rates. Their high thermal stability was determined

  烷基取代的二茂铁可以有效地催化复合固体推进剂的燃烧。但是，这些非极性和挥发性的二茂铁在长时间储存​​期间会迁移到推进剂表面，这会改变设计的燃烧参数，并更严重地引起意外爆炸。为了解决这个问题，合成了十二种带有甲基咪唑鎓和甲基三唑鎓取代基以及硝酸根和苦味酸根阴离子的离子二茂铁衍生物，作为新型的基于离子二茂铁的燃烧速率催化剂。通过1 H NMR，13 C NMR和元素分析对化合物进行了充分表征。其中十个通过单晶X射线衍射表征。化合物2和3在单斜空间群P 2（1）/ n和P 2（1）/ c中结晶。化合物4 ·H 2 O，6 ·1 / 2H 2 O，8-10和12在三斜空间群P中结晶。化合物7和11在正交空间群Pna 21和Pna中结晶2（1）。循环伏安法研究表明，所有化合物均表现出准可逆的氧化还原系统。迁移研究证实，这些离子二茂铁的迁移比2，2-双（乙基二茂铁基）丙烷的迁移慢得多。化合物的迁移趋势