5-(4-chloro-phenoxy)-1H-tetrazole | 4611-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-chloro-phenoxy)-1H-tetrazole
• 英文别名: 5-(4-Chlorophenoxy)tetrazole；5-(4-chlorophenoxy)-2H-tetrazole
• CAS: 4611-43-2
• 化学式: C₇H₅ClN₄O
• 分子量: 196.596
• InChiKey: FIPDALNPWLQCPP-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  360.6±44.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-chloro-phenoxy)-1H-tetrazole 、 氯甲酸甲酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到2-methoxycarbonyl-5-(p-chlorophenoxy)tetrazole
  参考文献：
  名称：

  摘要：

  The kinetics and mechanism of the N-2-N-1-isomerization of 2-methoxycarbonyl-5-(p-X-phenoxy)tetrazoles (X = H, CH3, NHCOCH3, Cl, Br, NO,) were studied by H-1 NMR spectroscopy in a DMSO-d(6)-CDCl3 mixture (25: 75). The rate of isomerization of the N-2-isomer into N-1-isomer fit the first-order equation (after three half-conversion periods). The isomerization is accompanied by hydrolysis and decarboxylation. The Hammett plot of ln(k(x)/k(H)) for the isomerization showed a good correlation with sigma(-) values (p(-) = 1.33, r = 0.965). A poor correlation with sigma values was obtained. The kinetic data, the effect of solvent polarity, the substituent effects, and the results of AMI quantum-chemical calculations suggest an ionic mechanism of the isomerization in polar solvents and a concerted mechanism in nonpolar solvents.

  DOI：

  10.1023/a:1013947228772
• 作为产物：
  描述：

  4-chlorophenyl cyanate 在 sodium azide 、 cobalt ferrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 以79%的产率得到5-(4-chloro-phenoxy)-1H-tetrazole
  参考文献：
  名称：

  CoFe₂O₄ Nanoparticles as a Magnetically Recoverable and Reusable Catalyst for the Synthesis of Arylaminotetrazoles and 5-aryloxytetrazoles

  摘要：

  以纳米 CoFe2O4 作为可重复使用的高效异相催化剂，描述了一种从芳基氰化物或犬牙交错化合物合成 5-芳基氨基-1H-四唑（异构体 A）或 1-芳基-5-氨基-1H-四唑（异构体 B）和 5-芳氧基四唑的高效直接方法。异构体 A 是由芳基环上带有电子吸收取代基的芳基氰化物制得的，而异构体 B 则是由电子释放基团制得的。这种方法的显著优点是产率高、无需使用危险和有害的苯甲酸、操作步骤简单以及催化剂可回收和重复使用。

  DOI：

  10.3184/174751914x13871210981307

文献信息

• A Facile and Efficient Method for Synthesis of the Aryloxyimidoyl Azides
  作者：Abdoul Hossein Dabbagh、Ali Reza Modarresi-Alam

  DOI：10.3184/030823400103165653

  日期：2000.1

  A facile and efficient synthesis is introduced for the new aryloxyimidoyl azides in a quantitative yield.

  以定量收率引入了新的芳氧基亚氨酰基叠氮化物的简便有效的合成。
• A One‐Pot Synthesis of Aryl‐N‐[(4‐methylphenylsulfonyl)]‐N‐(triphenylphosphoranylidene)imidocarbamates from 5‐Aryloxytetrazoles
  作者：Ali Reza Modarresi‐Alam、Ferydoon Khamooshi

  DOI：10.1081/scc-120027246

  日期：2004.12.31

  A one-pot synthesis of imidoyl iminophosphoranes 6a-f from 5-aryloxytetrazoles 1a-f and toluenesulfonyl chloride 3 in the presence of triethylamine and triphenylphosphine is described.
• ——
  作者：H. A. Dabbagh、Ya. Mansoori

  DOI：10.1023/a:1013947228772

  日期：——

  The kinetics and mechanism of the N-2-N-1-isomerization of 2-methoxycarbonyl-5-(p-X-phenoxy)tetrazoles (X = H, CH3, NHCOCH3, Cl, Br, NO,) were studied by H-1 NMR spectroscopy in a DMSO-d(6)-CDCl3 mixture (25: 75). The rate of isomerization of the N-2-isomer into N-1-isomer fit the first-order equation (after three half-conversion periods). The isomerization is accompanied by hydrolysis and decarboxylation. The Hammett plot of ln(k(x)/k(H)) for the isomerization showed a good correlation with sigma(-) values (p(-) = 1.33, r = 0.965). A poor correlation with sigma values was obtained. The kinetic data, the effect of solvent polarity, the substituent effects, and the results of AMI quantum-chemical calculations suggest an ionic mechanism of the isomerization in polar solvents and a concerted mechanism in nonpolar solvents.
• CoFe₂O₄ Nanoparticles as a Magnetically Recoverable and Reusable Catalyst for the Synthesis of Arylaminotetrazoles and 5-aryloxytetrazoles
  作者：Siavash Bahari、Akbar Rezaei

  DOI：10.3184/174751914x13871210981307

  日期：2014.2

  An efficient and direct method is described for the synthesis of 5-arylamino-1 H-tetrazoles (Isomer A) or 1-aryl-5-amino-1 H-tetrazoles (Isomer B) and 5-aryloxytetrazoles from arylcyanamides or cynates with nano CoFe₂O₄ as a reusable and efficient heterogeneous catalyst. Isomer A was obtained from arylcyanamides carrying electron-withdrawing substituents on the aryl ring, while isomer B was produced with electron-releasing groups. The significant advantages of this methodology are high yields, elimination of dangerous and harmful hydrazoic acid, simple work-up procedure and the recovery and reusability of the catalyst.

  以纳米 CoFe2O4 作为可重复使用的高效异相催化剂，描述了一种从芳基氰化物或犬牙交错化合物合成 5-芳基氨基-1H-四唑（异构体 A）或 1-芳基-5-氨基-1H-四唑（异构体 B）和 5-芳氧基四唑的高效直接方法。异构体 A 是由芳基环上带有电子吸收取代基的芳基氰化物制得的，而异构体 B 则是由电子释放基团制得的。这种方法的显著优点是产率高、无需使用危险和有害的苯甲酸、操作步骤简单以及催化剂可回收和重复使用。