1-(2-甲氧基苯基)四唑 | 99584-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(2-甲氧基苯基)四唑
• 英文名称: 1-(2-methoxyphenyl)-1H-1,2,3,4-tetrazole
• 英文别名: 1-(2-methoxyphenyl)-1H-tetrazole；1-(2-methoxyphenyl)tetrazole
• CAS: 99584-32-4
• 化学式: C₈H₈N₄O
• mdl: MFCD04222117
• 分子量: 176.178
• InChiKey: BEDVZJJLXFRNSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-甲氧基苯基)四唑 在 sodium hydroxide 、 sodium azide 、 三乙胺 、 溶剂黄146 作用下， 以 二甲基亚砜 、 异丙醇 为溶剂， 反应 2.0h， 以71%的产率得到1-(2-methoxyphenyl)-1H-tetrazol-5-amine
  参考文献：
  名称：

  One-Pot Syntheses of 5-Amino-1-aryltetrazole Derivatives

  摘要：

  已开发出一种新颖简便的方法，将5-氨基和5-烷基氨基取代基引入到1-芳基四唑中。通过连续的开环、叠氮化和分子内环化反应，从相应的1-芳基四唑一锅获得了一系列5-氨基-1-芳基四唑。5-烷基氨基-1-芳基四唑是通过类似机制从1,4-二取代的四唑盐形成的。研究揭示了芳基取代基的性质和反应条件对中间体氨基叠氮盐分子内环化反应的区域选择性的影响。

  DOI：

  10.1055/s-2006-926403
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以79%的产率得到1-(2-甲氧基苯基)四唑
  参考文献：
  名称：

  Polymer-Supported Fe-Phthalocyanine Derived Heterogeneous Photo-Catalyst for the Synthesis of Tetrazoles Under Visible Light Irradiation

  摘要：

  Herein, a polymer supported Fe-Phthalocyanine entangled with carboxyl functionalized benzimidazolium moiety (PSFePcCFBM) explored as heterogenous photocatalyst, for regioselective synthesis of 1H-tetrazoles from sodium azide and other affordable substrates. The PSFePcCFBM displayed good to excellent yield of the product (79-91%) under visible light (5 W) irradiations using home-made photoreactor. The NaN3 acts as a nitrogen donor of tetrazoles ring as well as it convert aldehyde into isocyanide as one of the nitrogen sources. The catalyst could be recycled up to 5th run successfully without altering its catalytic activity. The small amount of the catalyst loading, extensive substrate range, ease of separation of the catalyst by simple filtration, less reaction time, simple workup procedure, and excellent product yield are the salient features of the investigated protocol.

  DOI：

  10.1007/s10562-020-03461-z

文献信息

• Building Heterocyclic Systems with RC(OR)2+ Carbocations in Recyclable Brønsted Acidic Ionic Liquids: Facile Synthesis of 1-Substituted 1H-1,2,3,4-Tetrazoles, Benzazoles and Other Ring Systems with CH(OEt)3 and EtC(OEt)3 in [EtNH3][NO3] and [PMIM(SO3H)][O
  作者：Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1002/ejoc.201100128

  日期：2011.5

  IL-1/CH(OEt) 3 . The latter was also formed from 2-aminobenzoic acid in IL-1/CH(OEt) 3 . Mechanistic implications are addressed. The reported protocols enable rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and reuse of the ILs.

  1-芳基/烷基-1H-1,2,3,4-四唑可以通过与TMSN 3 和CH(OEt) 3 反应，使用容易获得的、可回收的、布朗斯台德酸性从相应的胺在一锅反应中方便地合成离子液体 [EtNH 3] -[NO 3 ] IL-1 和 [PMIM(SO 3 H)][OTf] IL-2 在温和条件下以高收率。基于对比反应，虽然两种 IL 都是极好的促进剂，但使用 IL-2 可以在更短的反应时间和更高的产率下完成反应。在提供的 24 个实施例中，除了 2-氨基苯甲酸与 IL-2 形成四唑和 IL-1 形成 2-乙基喹唑啉-4(3H)-one 外，通过两种 IL 获得了相同的产物。通过从反应中排除 TMS-N 3，原位形成的 CH(OEt) 2 + 和 Et-C(OEt) 2 +（通过它们相应的原酸酯）在超声处理下与带有各种取代基的邻苯二胺、邻氨基苯硫酚和邻氨基苯酚反应，形成一系列广泛的苯并咪唑（苯并咪唑
• Synthesis of 1-substituted tetrazoles via the acid-catalyzed [3+2] cycloaddition between isocyanides and trimethylsilyl azide
  作者：Tienan Jin、Shin Kamijo、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2004.10.103

  日期：2004.12

  were synthesized via the [3+2] cycloaddition between isocyanides and trimethylsilyl azide in the presence of an acid catalyst and MeOH. Various 1-substituted tetrazoles were obtained in good to high yields. The reaction probably proceeds through the in situ formation of hydrazoic acid, followed by a successive [3+2] cycloaddition with the isocyanide activated by an acid.

  在酸催化剂和MeOH的存在下，通过[3 + 2]在异氰酸酯和三甲基甲硅烷基叠氮化物之间的环加成反应合成1-取代的四唑。以良好至高收率获得了各种1-取代的四唑。该反应可能通过原位形成肼酸而进行，然后依次进行[3 + 2]环加成，并用酸活化异氰酸酯。
• Synthetic manifestation of nitro substituted tetrazole-N-(hetero)aryl derivatives and energetic studies
  作者：Nagarjuna Kommu、M. Balaraju、Vikas D. Ghule、Akhila K. Sahoo

  DOI：10.1039/c6ta10621h

  日期：——

  substituted tetrazole-N-aryl/heteroaryl derivatives is discussed here. The energetic functional groups –NO2, –NHNO2 and –N3 are reliably inserted into the molecular backbone, making the tetrazole-N-aryl derivatives highly energetic and insensitive to heat and impact. For example, the tetrazole derivatives 7 and 8, bearing a –NO2 or a –NHNO2 group, exhibit energetic properties close to RDX, but with enhanced

  本文讨论了一种用于构建硝基取代的四唑-N-芳基/杂芳基衍生物的可行的经济高效的合成方法。高能官能团–NO 2，–NHNO 2和–N 3可靠地插入分子主链，使四唑-N-芳基衍生物具有高能且对热和冲击不敏感。例如，带有–NO 2或–NHNO 2的四唑衍生物7和8组，表现出接近RDX的能量性质，但增强了不敏感性。大多数合成的化合物显示出放热分解，因此可用于高能材料的应用。
• ALKOXYTETRAZOL-1-YLBENZALDEHYDE COMPOUND AND PROCESS FOR PRODUCING THE SAME
  申请人：TOYO KASEI KOGYO COMPANY LIMITED

  公开号：EP1650198A1

  公开（公告）日：2006-04-26

  The present invention relates to a process for producing an alkoxy-(tetrazol-1-yl)benzaldehyde compound represented by Formula (2): wherein A1 is an alkoxy group, and A2 is a hydrogen atom, alkyl group or fluorine-substituted alkyl group, the process comprising reacting a 1-(alkoxyphenyl)-1H-tetrazole compound represented by Formula (1): wherein A1 and A2 are as defined above, with hexamethylenetetramine in a sulfonic acid solvent, followed by hydrolysis. According to the present invention, an alkoxy-(tetrazol-1-yl)benzaldehyde compound can be safely and efficiently produced by formylating a 1-(alkoxyphenyl)-1H-tetrazole compound.

  本发明涉及一种生产由式（2）表示的烷氧基（四唑-1-基）苯甲醛化合物的工艺： 其中 A1 是烷氧基，A2 是氢原子、烷基或氟取代的烷基，该工艺包括使式 (1) 所代表的 1-(烷氧基苯基)-1H-四唑化合物反应： 其中 A1 和 A2 如上定义，与六亚甲基四胺在磺酸溶剂中反应，然后水解。根据本发明，通过对 1-(烷氧基苯基)-1H-四唑化合物进行甲酰化，可以安全有效地制得烷氧基-(四唑-1-基)苯甲醛化合物。
• Indium triflate-catalyzed one-pot synthesis of 1-substituted-1H-1,2,3,4-tetrazoles under solvent-free conditions
  作者：Dhiman Kundu、Adinath Majee、Alakananda Hajra

  DOI：10.1016/j.tetlet.2009.03.131

  日期：2009.6

  A simple, efficient, and general method has been developed for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation of amine, trimethyl orthoformate, and sodium azide in presence of a catalytic amount of indium triflate under solvent-free conditions. The reaction proceeds smoothly to generate the corresponding 1-substituted tetrazoles in moderate to excellent yields under heating. (C) 2009 Elsevier Ltd. All rights reserved.