2-chloromethyl-1-methylbenzimidazole hydrochloride | 19412-48-7

• 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: 2-chloromethyl-1-methylbenzimidazole hydrochloride
• 英文别名: 2-chloromethyl-N-methylbenzimidazole hydrochloride；2-chloromethyl-1-methyl-1H-benzimidazole hydrochloride；2-(chloromethyl)-1-methyl-1H-benzimidazole hydrochloride；2-(chloromethyl)-1-methylbenzimidazole;hydrochloride
• CAS: 19412-48-7
• 化学式: C₉H₉ClN₂*ClH
• mdl: MFCD16040123
• 分子量: 217.098
• InChiKey: GZPFUBWTJVWDQM-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  17.8
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P330,P332+P313,P362,P403+P233,P405,P501
• 危险品运输编号：
  1759
• 危险性描述：
  H302,H315,H318,H335
• 储存条件：
  储存条件：2-8℃，密封保存，并确保干燥。

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-1-methylbenzimidazole hydrochloride 生成 2-(氯甲基)-1-甲基-1H-苯并咪唑
  参考文献：
  名称：

  WILSON, J. G.;HUNT, F. C., AUSTRAL. J. CHEM., 1983, 36, N 11, 2317-2325

  摘要：

  DOI：
• 作为产物：
  描述：

  羟基乙酸 、 N-methylbenzene-1,2-diamine dihydrochloride 在 盐酸 、 氯化亚砜 作用下， 生成 2-chloromethyl-1-methylbenzimidazole hydrochloride
  参考文献：
  名称：

  Structure, spectra and redox behaviour of copper(II) complexes of bis(benzimidazolyl)diamine ligands

  摘要：

  The linear quadridentate ligand N,N'-bis(benzimidazol-2-ylethyl)ethane-1,2-diamine (L1) and its 1-methylbenzimidazole analogue (L2) and homologues form 1:1 complexes with Cu (ClO4)2; L1 also forms complexes of the types CuL1X2 where X = NO3, PF6, Br or Cl and CuL1(X)Y where X = Cl or Br and Y = ClO4 or Br. Deep blue CuL1Br2.2H2O crystallizes in the monoclinic space group C2/c with Z = 4, a = 9.919(2), b = 16.626(3), c = 14.102(3) angstrom and beta = 94.39(2)-degrees. The structure was solved by Patterson and Fourier difference methods and refined by the least-squares technique to R = 0.064 for 2195 independent reflections with / > 1.5sigma(/). The molecule lies on a two-fold axis symmetrically around Cu(II). The co-ordination around Cu(II) is found to be square planar with two amino nitrogens and two benzimidazole nitrogens forming the equatorial plane [Cu-N 1.983(3) and 2.037(4) angstrom]. The bromides are at longer distances [3.349(1) angstrom] in axial sites. Ligand field and EPR spectra indicate that one bromide or chloride ion is axially co-ordinated to Cu(II) in [CuL1]2+. This ion exhibits quasi-reversible redox behaviour. Electrochemical studies of the dihalides in methanol have established the presence of [CuL1X2], [CuL1(X)]+ and [CuL1]2+ in equilibrium. In complexes with 565 [CuL4]2+ [L4 = N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine] and 555 [CuL3]2+ [L3 = N,N'-bis(1-methylbenzimidazol-2-ylmethyl)propane-1,3-diamine] chelate rings, Cu(II) does not seem to lie in the N4 square plane, as revealed by their low A(parallel-to) values and irreversible electrochemical behaviour. The Cu(II)-Cu(I) redox potentials in methanol are in the order [CuL1]2+ < [CuL3]2+ < [CuL4]2+; this illustrates that six-membered chelate rings are suitable to stabilize Cu(II), when Cu-N sigma interactions are favourable.

  DOI：

  10.1039/dt9920003377

文献信息

• High Resolution Scanning Tunneling Microscopy of a 1D Coordination Polymer with Imidazole-Based<i>N,N,O</i>Ligands on HOPG
  作者：Nina V. Fischer、Utpal Mitra、Karl-Georg Warnick、Viacheslav Dremov、Michael Stocker、Thorsten Wölfle、Wolfgang Hieringer、Frank W. Heinemann、Nicolai Burzlaff、Andreas Görling、Paul Müller

  DOI：10.1002/chem.201302379

  日期：2014.9.8

  Novel κ3‐N,N,O ligands tend to form 1D coordination polymer strands. Deposition of 1D structures on highly oriented pyrolytic graphite (HOPG) was achieved from diluted solutions and polymer strands have been studied on HOPG by AFM/STM. Single strands were mapped by STM and their electronic properties were subsequently characterized by current imaging tunneling spectroscopy (CITS). Periodic density

  新颖κ 3 - Ñ，Ñ，ö配体倾向于形成一维配位聚合物链。通过稀释溶液可在高取向热解石墨（HOPG）上沉积一维结构，并通过AFM / STM在HOPG上研究了聚合物链。单链通过STM绘制图谱，其电子特性随后通过电流成像隧道光谱（CITS）进行表征。模拟沉积在HOPG表面的聚合物链的周期性密度泛函计算与实验结果表明的之字形结构一致。观察到的周期性和Zn-Zn距离都可以在模拟中再现。发现范德华相互作用对分离的聚合物链的几何形状，HOPG的吸附几何形状以及吸附能量起着重要作用。
• Heteroaromatic pentacyclic compound and medicinal use thereof
  申请人：Ikemoto Tomoyuki

  公开号：US20060122181A1

  公开（公告）日：2006-06-08

  A 5-membered heteroaromatic ring compound represented by the formula [I] wherein V is CH or N; W is S or O; R 1 and R 2 are each H etc.; X is —N(R 4 )—, —O—, —S—, —SO 2 —N(R 5 )—, —CO—N(R 7 )— etc.; L is wherein R 20 , R 21 , R 22 and R 25 are each H etc.; E is aryl or heteroaromatic ring group; R is —COOH etc.; B is aryl etc.; R 3 is H etc.; Y is —C(R 13 )(R 14 )—N(R 12 )—C(R 13 )(R 14 )—O—, —N(R 11 )—, —O— etc.; A is alkylene; and Z is aryl etc., a prodrug thereof and a pharmaceutically acceptable salt thereof. The compound [I] has a superior protein tyrosine phosphatase 1B inhibitory activity and is useful as a therapeutic agent for diabetes, diabetic complications, hyperlipidemia, obesity and the like.

  一种由公式[I]表示的五元杂环芳香环化合物，其中V为CH或N；W为S或O；R1和R2分别为H等；X为—N(R4)—，—O—，—S—，—SO2—N(R5)—，—CO—N(R7)—等；L为其中R20，R21，R22和R25分别为H等的基团；E为芳基或杂环芳香基团；R为—COOH等；B为芳基等；R3为H等；Y为—C(R13)(R14)—N(R12)—C(R13)(R14)—O—，—N(R11)—，—O—等；A为烷基；Z为芳基等，其前药和药学上可接受的盐。该化合物[I]具有优越的蛋白酪氨酸磷酸酶1B抑制活性，并可用作治疗糖尿病、糖尿病并发症、高脂血症、肥胖症等的治疗剂。
• HETEROAROMATIC PENTACYCLIC COMPOUND AND MEDICINAL USE THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP1553091A1

  公开（公告）日：2005-07-13

  A 5-membered heteroaromatic ring compound represented by the formula [I] wherein V is CH or N; W is S or O; R1 and R2 are each H etc.; X is -N(R4)-, -O-, -S-, -SO2-N(R5)-, -CO-N(R7)- etc.; L is wherein R20, R21, R22 and R25 are each H etc.; E is aryl or heteroaromatic ring group; R is -COOH etc.; B is aryl etc.; R3 is H etc.; Y is -C(R13)(R14)-N(R12)-, -C(R13)(R14)-O-, -N(R11)-, -O- etc.; A is alkylene; and Z is aryl etc., a prodrug thereof and a pharmaceutically acceptable salt thereof. The compound [I] has a superior protein tyrosine phosphatase 1B inhibitory activity and is useful as a therapeutic agent for diabetes, diabetic complications, hyperlipidemia, obesity and the like.

  由式[I]代表的 5 元杂芳环化合物 其中 V 是 CH 或 N；W 是 S 或 O；R1 和 R2 各自是 H 等；X 是 -N(R4)-、-O-、-S-、-SO2-N(R5)-、-CO-N(R7)- 等；L 是 其中 R20、R21、R22 和 R25 各为 H 等；E 为芳基或杂芳环基团；R 为-COOH 等；B 为芳基等；R3 为 H 等；Y 为-C(R13)(R14)-N(R12)-、-C(R13)(R14)-O-、-N(R11)-、-O- 等；A 为亚烷基；Z 为芳基等、其原药及其药学上可接受的盐。 化合物[I]具有优异的蛋白酪氨酸磷酸酶 1B 抑制活性，可作为糖尿病、糖尿病并发症、高脂血症、肥胖症等的治疗剂。
• EP1553091
  申请人：——

  公开号：——

  公开（公告）日：——
• Structure, spectra and redox behaviour of copper(II) complexes of bis(benzimidazolyl)diamine ligands
  作者：Thangarasu Pandiyan、Mallayan Palaniandavar、M. Lakshminarayanan、Hattikudur Manohar

  DOI：10.1039/dt9920003377

  日期：——

  The linear quadridentate ligand N,N'-bis(benzimidazol-2-ylethyl)ethane-1,2-diamine (L1) and its 1-methylbenzimidazole analogue (L2) and homologues form 1:1 complexes with Cu (ClO4)2; L1 also forms complexes of the types CuL1X2 where X = NO3, PF6, Br or Cl and CuL1(X)Y where X = Cl or Br and Y = ClO4 or Br. Deep blue CuL1Br2.2H2O crystallizes in the monoclinic space group C2/c with Z = 4, a = 9.919(2), b = 16.626(3), c = 14.102(3) angstrom and beta = 94.39(2)-degrees. The structure was solved by Patterson and Fourier difference methods and refined by the least-squares technique to R = 0.064 for 2195 independent reflections with / > 1.5sigma(/). The molecule lies on a two-fold axis symmetrically around Cu(II). The co-ordination around Cu(II) is found to be square planar with two amino nitrogens and two benzimidazole nitrogens forming the equatorial plane [Cu-N 1.983(3) and 2.037(4) angstrom]. The bromides are at longer distances [3.349(1) angstrom] in axial sites. Ligand field and EPR spectra indicate that one bromide or chloride ion is axially co-ordinated to Cu(II) in [CuL1]2+. This ion exhibits quasi-reversible redox behaviour. Electrochemical studies of the dihalides in methanol have established the presence of [CuL1X2], [CuL1(X)]+ and [CuL1]2+ in equilibrium. In complexes with 565 [CuL4]2+ [L4 = N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine] and 555 [CuL3]2+ [L3 = N,N'-bis(1-methylbenzimidazol-2-ylmethyl)propane-1,3-diamine] chelate rings, Cu(II) does not seem to lie in the N4 square plane, as revealed by their low A(parallel-to) values and irreversible electrochemical behaviour. The Cu(II)-Cu(I) redox potentials in methanol are in the order [CuL1]2+ < [CuL3]2+ < [CuL4]2+; this illustrates that six-membered chelate rings are suitable to stabilize Cu(II), when Cu-N sigma interactions are favourable.