5-(2-nitro-4-methylphenyl)-1H-1,2,3,4-tetrazole | 1357488-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2-nitro-4-methylphenyl)-1H-1,2,3,4-tetrazole
• 英文别名: 5-(2-nitro-p-tolyl)-1H-tetrazole；5-(4-methyl-2-nitrophenyl)-2H-tetrazole
• CAS: 1357488-40-4
• 化学式: C₈H₇N₅O₂
• 分子量: 205.176
• InChiKey: RBAQXXRXXQKRKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲基-2-硝基苯腈 在 indium(III) chloride 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.2h， 以70%的产率得到5-(2-nitro-4-methylphenyl)-1H-1,2,3,4-tetrazole
  参考文献：
  名称：

  InCl₃-Catalyzed [2+3] Cycloaddition Reaction: A Rapid Synthesis of 5-Substituted 1H-tetrazole under Microwave Irradiation

  摘要：

  一系列5-取代的1H-四氮唑通过InCl3催化（10 mol％）在微波辐射的影响下，从结构上不同的有机腈与偏硝基钠反应，高效地制备出来。该方法成功应用于脂肪族，芳香族，苄基和杂环腈，得到了良好至优异的产率（70-96％）的对应5-取代的1H-四氮唑。这种方法具有显着的优势，如反应时间短，操作简单，经济效益显著。

  DOI：

  10.1155/2012/615891

文献信息

• Fe ₃ O ₄ @L‐lysine‐Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5‐substituted 1H‐tetrazoles
  作者：Muhammad Aqeel Ashraf、Zhenling Liu、Cheng Li、Dangquan Zhang

  DOI：10.1002/aoc.6133

  日期：2021.3

  An efficient and sustainable synthetic protocol has been presented to synthesis and 5‐substituted 1H‐tetrazole privileged heterocyclic substructures. The synthetic protocol involves two‐component reaction between aryl nitriles and NaN3 in water using complex of L‐lysine‐palladium nanoparticles (NPs) modified Fe3O4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst

  已经提出了一种有效且可持续的合成方案，用于合成和5取代的1H-四唑特权杂环亚结构。合成方案涉及使用L-赖氨酸-钯纳米粒子（NPs）修饰的Fe 3 O 4纳米粒子复合物作为磁性可分离，可回收和可重复使用的多相催化剂，使芳基腈与水中的NaN 3之间发生两组分反应。磁性可回收L-赖氨酸-Pd（0）修饰的Fe 3 O 4纳米粒子被用于5个取代的1H-四唑的[2 + 3]环加成合成中。该策略的优势包括昂贵的Pd NP的易于回收和有效的可重复使用性，[2 + 3]环加成的高收率，较短的反应时间，并且所有报道的合成策略都在水中作为绿色溶剂广泛应用基材范围。
• Glycerol mediated synthesis of 5-substituted 1H-tetrazole under catalyst free conditions
  作者：Kamalakar P. Nandre、Jagdish K. Salunke、Jitendra P. Nandre、Vijay S. Patil、Amul U. Borse、Sidhanath V. Bhosale

  DOI：10.1016/j.cclet.2011.11.019

  日期：2012.2

  We have developed simple, cost effective and environmentally benign protocol for the synthesis of 5-substituted 1H-tetrazoles via [2,3] cycloaddition reaction from organic nitriles and sodium azide in glycerol under catalyst free condition. The corresponding 5-substituted 1H-tetrazoles were obtained with good to excellent yields (68-95%). (C) 2011 Sidhanath V. Bhosale. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Green Synthesis of 5-Substituted-1H-1,2,3,4-tetrazoles and 1-Sustituted-1H-1,2,3,4-tetrazoles via [3+2] Cycloaddition by Reusable Immobilized AlCl3 on γ-Al2O3
  作者：Hemmaragala Marishetty Nanjundaswamy、Heidi Abrahamse

  DOI：10.3987/com-14-13048

  日期：——

  We report the effectiveness of the surface modified gamma-Al2O3 which is reusable, efficient, catalytic, safe and environmentally acceptable procedure for the conversion of both alkyl and aryl nitriles into the corresponding 5-substituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition with sodium azide in excellent yields at mild reaction conditions (50 degrees C). The catalyst also afforded 1-substituted-1H-1,2,3,4-tetrazoles by the reaction of amines, sodium azide and triethyl orthoformate. The catalyst could be recycled and was reused eleven runs without losing its activity.