5-(p-tolyl)amino-1H-tetrazole | 117891-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(p-tolyl)amino-1H-tetrazole
• 英文别名: (1H-tetrazol-5-yl)-p-tolyl-amine；N-(4-methylphenyl)-2H-tetrazol-5-amine
• CAS: 117891-43-7
• 化学式: C₈H₉N₅
• 分子量: 175.193
• InChiKey: AZZAOUBUEBZZIP-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  355.1±35.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(p-tolyl)amino-1H-tetrazole 生成 1-(4-甲基苯基)四唑-5-胺
  参考文献：
  名称：

  Thermal Isomerization of Substituted 5-Aminotetrazoles¹

  摘要：

  DOI：

  10.1021/ja01630a024
• 作为产物：
  描述：

  1-(4-甲基苯基)四唑-5-胺 以 乙二醇 为溶剂， 生成 5-(p-tolyl)amino-1H-tetrazole
  参考文献：
  名称：

  Schelenz, Thomas; Schaefer, Wieland, Advanced Synthesis and Catalysis, 2000, vol. 342, # 2, p. 197 - 200

  摘要：

  DOI：

文献信息

• l-Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1H-Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide
  作者：Vikas Telvekar、Saket Bhagat

  DOI：10.1055/s-0036-1591534

  日期：2018.4

  A simple and efficient route for the synthesis of a series of 5-substituted 1H-tetrazoles using l -proline as a catalyst from structurally diverse organic nitriles and sodium azide is reported. The prominent features of this environmentally benign, cost effective, and high-yielding l -proline-catalyzed protocol includes simple experimental procedure, short reaction time, simple workup, and excellent

  报道了使用 l-脯氨酸作为催化剂从结构多样的有机腈和叠氮化钠合成一系列 5-取代 1H-四唑的简单有效的途径。这种环境友好、成本效益高且产率高的 l-脯氨酸催化方案的突出特点包括简单的实验程序、较短的反应时间、简单的后处理和优异的产率，使其成为危险的路易斯酸催化方法的更安全、更经济的替代方案。该协议已成功应用于广泛的基材，包括脂肪族和芳基腈、有机硫氰酸盐和氰胺。
• Solvent-free preparation of arylaminotetrazole derivatives using aluminum(III) hydrogensulfate as an effective catalyst
  作者：Ferydoon Khamooshi、Ali Reza Modarresi-Alam

  DOI：10.1016/j.cclet.2010.03.008

  日期：2010.8

  Abstract An efficient and simple method for the preparation of 5-arylamino-1H-tetrazole and 1-aryl-5-amino-1H-tetrazole derivatives is reported using aluminum(III) hydrogensulfate (Al(HSO4)3) as an effective heterogeneous catalyst from secondary arylcyanamides. Generally, when the substitution in arylcyanamide is strongly electron-withdrawing the position of equilibrium would shift toward the isomer

  摘要报道了以硫酸铝（III）（Al（HSO4）3）为有效多相催化剂制备5-芳基氨基-1H-四唑和1-芳基-5-氨基-1H-四唑衍生物的简便方法。来自仲芳基氰酰胺。通常，当芳基氰酰胺中的取代强烈吸电子时，平衡的位置将移向1-芳基-5-氨基-1H-四唑（B）的异构体，并且随着取代基的电子给体的增加，平衡的位置转移到5-芳基氨基-1H-四唑（A）的异构体上。本方法学具有几个优点，例如优异的收率，较短的反应时间，易于后处理和较绿的条件。
• Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene
  作者：Dasharath D. Kondhare、Venkat V. Bhadke、Sushma S. Deshmukh、Mahesh G. Wakhradkar、Balaji B. Totawar

  DOI：10.1016/j.jics.2021.100103

  日期：2021.8
• Synthesis of arylaminotetrazoles by ZnCl2/AlCl3/silica as an efficient heterogeneous catalyst
  作者：Davood Habibi、Mahmoud Nasrollahzadeh

  DOI：10.1007/s00706-011-0670-8

  日期：2012.6

  Arylaminotetrazoles were efficiently synthesized from secondary arylcyanamides by application of ZnCl2/AlCl3/silica as a reusable heterogeneous Lewis acid catalyst. 5-Arylamino-1-tetrazoles can be obtained from arylcyanamides carrying electron-withdrawing substituents on the aryl ring, while with electron-releasing groups 1-aryl-5-amino-1-tetrazoles will be produced. The former isomer is also produced within longer reaction times (similar to 20 h) even with electron-releasing groups.
• Kinetics of the Isomerization of Substituted 5-Aminotetrazoles
  作者：Ronald A. Henry、William G. Finnegan、Eugene Lieber

  DOI：10.1021/ja01613a071

  日期：1955.4