N-(benzimidazol-2-ylmethyl)iminodiacetic acid | 89218-91-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(benzimidazol-2-ylmethyl)iminodiacetic acid
• 英文别名: N-(2-benzimidazolyl)methyliminodiacetic acid；(1H-benzimidazol-2-ylmethylimino)-di-acetic acid；(1H-Benzimidazol-2-ylmethylimino)-di-essigsaeure；2,2'-{[(1H-Benzimidazol-2-yl)methyl]azanediyl}diacetic acid；2-[1H-benzimidazol-2-ylmethyl(carboxymethyl)amino]acetic acid
• CAS: 89218-91-7
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: INEZAVVPHRUSIC-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C
• 沸点：
  619.0±50.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonate)oxovanadium 、 N-(benzimidazol-2-ylmethyl)iminodiacetic acid 以 水 为溶剂， 以91%的产率得到
  参考文献：
  名称：

  Six-co-ordinated vanadium-(IV) and -(V) complexes of benzimidazole and pyridyl containing ligands

  摘要：

  制备了一系列新的钒-(IV)和钒-(V)配合物，其配体含有羟乙基、羧酸基、胺、吡啶基和苯并咪唑等官能团。三种配合物的晶体结构已经确定。所有的钒原子都是六配位的，尽管以前的二乙醇胺型复合物都含有五配位的钒。苯并咪唑络合物的 V-N（胺）键明显长于吡啶络合物。质子化配体的 pK a 值与相应钒-(IV)、-(V)和-(IV/V)络合物的 V-N（胺）键长度（反式至一个氧代基团）之间存在经验关系。光谱研究（核磁共振、电子显微镜和紫外/可见分光光度计）表明，这些配合物在水溶液中保持完整。一般来说，羟乙基取代的钒络合物不如相应的醋酸基取代的钒络合物稳定，苯并咪唑络合物不如相应的吡啶络合物稳定。对所有这些络合物性质的综合了解为设计与生物应用相关的新钒络合物提供了一个极好的平台。

  DOI：

  10.1039/a700710h
• 作为产物：
  描述：

  2-氯甲基苯并咪唑 生成 N-(benzimidazol-2-ylmethyl)iminodiacetic acid
  参考文献：
  名称：

  454.一些潜在的螯合剂，衍生自苯并咪唑

  摘要：

  DOI：

  10.1039/jr9590002296

文献信息

• Iminodiacetic acid derivatives of benzimidazole. Synthesis of N-(Benzimidazol-2-ylmethyl)iminodiacetic acids
  作者：JG Wilson、FC Hunt

  DOI：10.1071/ch9832317

  日期：——

  Ten new N-(2-benzimidazolylmethyl)iminodiacetic acids (BIMIDA)* have been synthesized from the corresponding o-phenylenediamines via intermediate 2-chloromethyl and 2-aminomethyl benzimid- azoles as ligands for 99mTc. Anomalies associated with the synthesis of the iodo-substituted compound are described.

  十种新的 N-(2-苯并咪唑甲基)亚氨基二乙酸 (BIMIDA)* 从相应的邻苯二胺中合成出来。 合成了十种新的 N-(2-苯并咪唑甲基)亚氨基二乙酸 (BIMIDA) 通过中间体 2-氯甲基和 2-氨基甲基苯并咪唑合成了十种新的 N-(2-苯并咪唑基甲基)亚氨基二乙酸 (BIMIDA) 作为 99mTc 的配体。与合成 描述了与碘代化合物合成有关的异常现象。
• Equilibrium and structural studies on Co(II), Ni(II), Cu(II) and Zn(II) complexes with N-(2-benzimidazolyl)methyliminodiacetic acid: crystal structures of Ni(II) and Cu(II) complexes
  作者：Susmita Bandyopadhyay、Ansuman Das、G.N. Mukherjee、Andrea Cantoni、Gabriele Bocelli、Siddhartha Chaudhuri、Joan Ribas

  DOI：10.1016/j.ica.2004.05.010

  日期：2004.9

  for M = Co and Zn, n=2 for M = Ni) and Cu (μ-L) · 4H2O}n, have been isolated and characterized by elemental analysis, spectral, conductance and magnetic measurements and thermal studies. Structures of [Ni(L)(H2O)2] · 2H2O and Cu(μ-L) · 4H2O}n have been determined by single crystal X-ray diffraction. The nickel(II) complex exists in a distorted octahedral environment in which the metal ion is coordinated

  结合pH值，UV-Vis，1 H NMR和EPR光谱研究M（II）离子（M = Co，Ni，Cu和Zn）与N-（2-苯并咪唑基）甲基亚氨基二乙酸（H 2）的络合物形成bzimida（以下称H 2 L）在水溶液中以固定的离子强度（I = 10 -1 mol dm -3）在25±1°C表示形成M（L），M（H -1 L）-和M 2（H -1 L）+配合物。质子-配体和金属-配体常数以及复合物的形成平衡已经阐明。固体络合物，[M（L）（H 2 O）2 ]· Ñ ħ 2 O（Ñ对于M = Co和Zn，= 1 ñ = 2 M = Ni）和的Cu（μ-L）·4H 2 ö} Ñ，已被分离和表征通过元素分析，光谱，电导以及磁测量和热研究。[Ni（L）（H 2 O）2 ]·2H 2 O和Cu（μ-L）·4H 2 O} n的结构已经通过单晶X射线衍射确定。镍（II）配合物存在于扭曲的八面体环境中，其中金属
• Synthesis and characterization of a bis-μ,η1-carboxylate-bridged dinuclear manganese(II) complex containing a tetradentate tripodal ligand, N-(benzimidazol-2-ylmethyl)iminodiacetic acid
  作者：Dohyun Moon、Junghyun Kim、Minhak Oh、Byoung Jin Suh、Myoung Soo Lah

  DOI：10.1016/j.poly.2007.09.028

  日期：2008.1

  The dinuclear Mn(II) complex, [Mn 2 (Hbida) 2 (H 2 O) 2 ], was prepared using a tetradentate tripodal ligand, N -(benzimidazol-2-ylmethyl)iminodiacetic acid (H 3 bida) which has two carboxylate and one benzimidazole groups. The manganese ions are doubly bridged using μ,η 1 -bridging monodentate carboxylate oxygen atoms. The Mn–Mn bond distance of 3.446 A in the complex is comparable to that observed

  双核Mn（II）配合物[Mn 2（Hbida）2（H 2 O）2]是使用四齿三脚架配体N-（苯并咪唑-2-基甲基）亚氨基二乙酸（H 3 bida）制备的羧酸盐和一个苯并咪唑基团。锰离子使用μ，η1-桥联单齿羧酸盐氧原子双桥联。复合物中的Mn-Mn键距离为3.446 A，与在天然锰精氨酸酶的活性位点（3.30 A）中观察到的相当。具有四种羧酸盐的复合物的几何结构以两种不同类型的结合模式（非桥连单齿和μ，η1型桥连单齿）模拟了锰精氨酸酶的活性位点结构。该复合物的磁性能显示出耦合常数J = -0.471（1）cm -1，与弱耦合反铁磁Mn II（S = 5/2）中心一致。
• Structural and equilibrium studies on mixed ligand complexes of Co(II), Ni(II), Cu(II) and Zn(II) with N-(2-benzimidazolyl)methyliminodiacetic acid and typical N,N donor ligands
  作者：Susmita Bandyopadhyay、G.N. Mukherjee、M.G.B. Drew

  DOI：10.1016/j.ica.2005.06.008

  日期：2005.9

  Mixed ligand complexes: [Co(L)(bipy)] (.) 3H(2)O (1), [Ni(L)(phen)] (.) H2O (2), [Cu(L)(phen)] (.) 3H(2)O (3) and [Zn(L)(bipy)] (.) 3H(2)O (4), where L2- = two -COOH deprotonated dianion of N-(2-benzimidazolyl)methyliminodiacetic acid (H(2)bzimida, hereafter, H,L), bipy = 2,2' bipyridine and phen = 1,10-phenanthroline have been isolated and characterized by elemental analysis, spectral and magnetic measurements and thermal studies. Single crystal X-ray diffraction studies show octahedral geometry for 1, 2 and 4 and square pyramidal geometry for 3. Equilibrium studies in aqueous solution (ionic strength I = 10(-1) mol dm(-3) (NaNO3), at 25 +/- 1 degrees C) using different molar proportions of M(II):H2L:B, where M = Co, Ni, Cu and Zn and B = phen, bipy and en (ethylene diamine), however, provides evidence of formation of mononuclear and binuclear binary and mixed ligand complexes: M(L), M(H-1L)(-), M(B)(2+), M(L)(B), M(H-1L)(B)(-), M-2(H-1L)(OH), (B)M(H-1L)M(B)(+), where H-1L3- represents two -COOH and the benzimidazole NI-H deprotonated quadridentate (O-, N, O-, N), or, quinquedentate (O-, N, O-, N, N-) function of the coordinated ligand H,L. Binuclear mixed ligand complex formation equilibria: M(L)(B) + M(B)(2+) = (B)M(H-1L)M(B)(+) + H+ is favoured with higher pi-acidity of the B ligands. For Co(II), Ni(II) and Cu(II), these equilibria are accompanied by blue shift of the electronic absorption maxima of M(II) ions, as a negatively charged bridging benzimidazolate moiety provides stronger ligand field than a neutral one. Solution stability of the mixed ligand complexes are in the expected order: Co(II) < Ni(II) < Cu(II) > Zn(II). The Delta logK(M) values are less negetive than their statistical values, indicating favoured formation of the mixed ligand complexes over the binary ones. (c) 2005 Elsevier B.V. All rights reserved.
• WILSON, J. G.;HUNT, F. C., AUSTRAL. J. CHEM., 1983, 36, N 11, 2317-2325
  作者：WILSON, J. G.、HUNT, F. C.

  DOI：——

  日期：——