bis(benzimidazol-2-ylmethyl)methylamine | 132625-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: bis(benzimidazol-2-ylmethyl)methylamine
• 英文别名: N,N-bis(1-methylbenzimidazol-2-ylmethyl)methylamine；N,N-bis(2-(1-Me-benzimidazol-2-yl)methyl)-N-(methyl)amine；N,N-bis((1-methyl-benzimidazol-2-yl)methyl)-N-methylamine；N-methyl-N,N-bis[(1-methyl-1H-benzimidazol-2-yl)methyl]amine；N-bis(1-methylbenzimidazol-2-ylmethyl)methylamine；N-methyl-1-(1-methylbenzimidazol-2-yl)-N-[(1-methylbenzimidazol-2-yl)methyl]methanamine
• CAS: 132625-06-0
• 化学式: C₁₉H₂₁N₅
• 分子量: 319.409
• InChiKey: ZMUGLQXCFRDXMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trichlorotris(tetrahydrofuran)chromium(III) 、 bis(benzimidazol-2-ylmethyl)methylamine 以 四氢呋喃 为溶剂， 反应 12.0h， 以85.8%的产率得到N-methyl-1-(1-methylbenzimidazol-2-yl)-N-[(1-methylbenzimidazol-2-yl)methyl]methanamine;trichlorochromium
  参考文献：
  名称：

  Alternating α-Olefin Distributions via Single and Double Insertions in Chromium-Catalyzed Ethylene Oligomerization

  摘要：

  The catalytic oligomerization of ethylene with chromium-based complexes containing bis(benzimidazolemethyl)amine (BIMA) ligands results in alternating distributions of linear alpha-olefins (LAOs). Extremely high activities are obtained (>100 000 g mmol(-1) h(-1) bar(-1)) with N-alkyl-substituted BIMA ligands, whereas bulky groups on the central nitrogen or alternative central donors result in much lower activities. Variations in the ligand backbone, as well as methylation of the benzimidazole units, lead to reduction in activity. The alternating LAO distributions have been mathematically analyzed using second -order recurrence relations. The shape of the distributions is affected by ethylene pressure (1-4 bar) and by the cocatalyst to some degree. On the basis of the results and analysis presented herein, we propose that the alternating behavior originates from the ability of these chromium BIMA catalysts to undergo single as well as double ethylene insertion reactions. A minor second distribution (<5 wt %) of 2-ethyl-1-alkenes is obtained under certain conditions, resulting from incorporation of 1-butene. DFT studies (MO6L) and experimental observations regarding the reaction between AIMe(3) and the N-methyl BIMA ligand 2 have shown that deprotonation of the benzimidazole N-H units can occur, which suggests a change in coordination of the BIMA ligand under oligomerization conditions.

  DOI：

  10.1021/acs.organomet.6b00671
• 作为产物：
  描述：

  N,N-bis((1H-benzimidazol-2-yl)methyl)-N-methylamine 在 NaH 、 碘甲烷 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 bis(benzimidazol-2-ylmethyl)methylamine
  参考文献：
  名称：

  Polymerisation and oligomerisation catalysts

  摘要：

  一种聚合催化剂，包括（1）式A的过渡金属化合物，和可选的（2）Lewis酸活化剂，式（A），其中Z是一个含有至少一个碳原子、至少一个氮原子和至少一个其他来自氮、硫和氧的杂原子的五元杂环基团，环中剩余的原子为氮或碳；M是周期表3至11族元素或镧系金属；E1和E2是来自（i）脂肪烃、（ii）脂环烃、（iii）芳香烃、（iv）烷基取代的芳香烃、（v）杂环基团和（vi）（i）至（v）中的杂取代衍生物的二价基团；D′和D2是给体基团；X是一个阴离子基团，L是一个中性给体基团；n=m=零或1；y和z为零或整数。这些催化剂可用于聚合或寡聚1-烯烃。

  公开号：

  US20060094588A1

文献信息

• Nickel(II) Dibromide Complexes Bearing Bis(benzimidazolyl)amine and Bis(benzimidazolyl)pyridine Ligands for Ethylene Oligomerizations
  作者：Gyeong Mi Lee、Vinu K. Appukuttan、Hongsuk Suh、Chang-Sik Ha、Il Kim

  DOI：10.1007/s10562-011-0697-9

  日期：2011.11

  and bis(benzimidazolyl)pyridine ligands and their respective nickel(II) dibromide complexes were synthesized and fully characterized. After activation of the nickel complexes with ethylaluminum sesquichloride showed productivity in excess of 106 (g-oligomer)(mol-Ni)−1h−1bar−1 towards ethylene oligomerization, producing butenes as major products. The bis(benzimidazolyl)pyridine nickel complexes showed

  合成并充分表征了一系列双（苯并咪唑基）胺和双（苯并咪唑基）吡啶配体及其各自的二溴化镍（II）配合物。镍配合物与乙基铝倍半氯化物活化后显示出超过 106 (g-低聚物)(mol-Ni)-1h-1bar-1 的生产率，用于乙烯低聚，生产丁烯作为主要产品。双（苯并咪唑基）吡啶镍配合物比相应的双（苯并咪唑基）胺镍配合物显示出更高的活性和二聚选择性。
• The effect of the central donor in bis(benzimidazole)-based cobalt catalysts for the selective cis-1,4-polymerisation of butadiene
  作者：Renan Cariou、Juan J. Chirinos、Vernon C. Gibson、Grant Jacobsen、Atanas K. Tomov、George J. P. Britovsek、Andrew J. P. White

  DOI：10.1039/c0dt00402b

  日期：——

  of bis(benzimidazole)-based cobalt(II) dichloride complexes containing a range of different central donors has been synthesized and characterized. The nature of the central donor affects the binding of the ligand to the cobalt centre and determines the coordination geometry of the metal complexes. All complexes have been shown to catalyse the polymerization of butadiene, in combination with MAO as

  一系列 双（苯并咪唑）-基于 二氯化钴已经合成并表征了包含一系列不同中央供体的复合物。中心给体的性质影响配体与钴中心的结合并确定金属配合物的配位几何形状。已证明所有配合物都可与丁二烯一起催化丁二烯的聚合。毛 作为助催化剂， 顺式-1,4-聚丁二烯具有高选择性。中心给体的性质对催化剂的聚合活性有显着影响，但不影响聚合物的微观结构。的加法PPh 3 通常会提高这些聚合物的聚合活性 钴 催化剂和结果主要（60–70％） 1,2-乙烯基-聚丁二烯。
• Tripodal benzimidazolate complexes of tricarbonylmolybdenum(0) and of iron(III)
  作者：Jonathan D. Crane、David E. Fenton

  DOI：10.1039/dt9900003647

  日期：——

  The reactions of the tripodal ligands N,N-bis(benzimidazol-2-ylmethyl)amine (L1), N,N-bis(benzimidazol-2-ylmethyl)methylamine (L2), and N,N-bis(1-methylbenzimidazol-2-ylmethyl)-methylamine (L3) with molybdenum hexacarbonyl and tris(acetonitrile)tricarbonylmolybdenum to give (benzimidazolato)tricarbonylmolybdenum complexes, and of L1 and L3 with iron (lll) salts to give di-iron(lll) complexes containing the [Fe2(mu-O)(mu-RCO2)2]2+ core are described. The application of the molybdenum complexes as i.r. spectroscopic probes for the ligand bands in the dinuclear species is reported, together with the mass spectra and electronic spectra of the di-iron(lll) species. The di-iron(lll) complexes show an ability to undergo carboxylate exchange reactions.
• POLYMERISATION AND OLIGOMERISATION CATALYSTS
  申请人：Innovene Europe Limited

  公开号：EP1603957A1

  公开（公告）日：2005-12-14
• US7229943B2
  申请人：——

  公开号：US7229943B2

  公开（公告）日：2007-06-12