4-methylbenzenediazonium trifluoromethanesulfonate | 96227-78-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 4-methylbenzenediazonium trifluoromethanesulfonate
• 英文别名: (p-toluene)diazonium trifluoromethanesulfonate；4-Methylbenzenediazonium;trifluoromethanesulfonate
• CAS: 96227-78-0
• 化学式: CF₃O₃S*C₇H₇N₂
• 分子量: 268.216
• InChiKey: JNBKBWMMNVROPK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methylbenzenediazonium trifluoromethanesulfonate 以 三氟乙酸 为溶剂， 以43%的产率得到对苄基三氟甲磺酸
  参考文献：
  名称：

  The sequel to a carbocyclic nucleoside synthesis: a divergent access to both arenediazonium ions and aryl triflates

  摘要：

  Depending on the amount of acid used, treating aryl-dialkyl triazenes of general structure 3 with triflic acid resulted in the formation of either the corresponding arenediazonium triflates 4 or aryl triflates 8 apparently by two different pathways, the latter conversion being favoured at high acid concentration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.147
• 作为产物：
  描述：

  (4-methylphenyl)-piperidin-1-yldiazene 、 三氟甲磺酸 以 乙酸乙酯 为溶剂， 以47%的产率得到4-methylbenzenediazonium trifluoromethanesulfonate
  参考文献：
  名称：

  The sequel to a carbocyclic nucleoside synthesis: a divergent access to both arenediazonium ions and aryl triflates

  摘要：

  Depending on the amount of acid used, treating aryl-dialkyl triazenes of general structure 3 with triflic acid resulted in the formation of either the corresponding arenediazonium triflates 4 or aryl triflates 8 apparently by two different pathways, the latter conversion being favoured at high acid concentration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.147

文献信息

• Synthesis of Acetamides from Aryl Amines and Acetonitrile by Diazotization under Metal-Free Conditions
  作者：Yao-Fu Zeng、Yi-Na Li、Na-Na Zhang、Huan Kang、Pan Duan、Fang Xiao、Yu Guo、Xianghao Wen

  DOI：10.1055/s-0039-1690237

  日期：2019.12

  An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.

  已开发出一种有效且无金属的偶联反应，可从相应的芳胺和乙腈中生成乙酰胺。该方法可耐受范围广泛的官能团，并且对芳基胺具有选择性。进行了初步的机理研究。
• Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts
  作者：Victor D. Filimonov、Elena A. Krasnokutskaya、Assia Zh. Kassanova、Valentina A. Fedorova、Ksenia S. Stankevich、Nikolay G. Naumov、Alexander A. Bondarev、Veronika A. Kataeva

  DOI：10.1002/ejoc.201800887

  日期：2019.1.31

  A variety of stable, safe, and soluble arenediazonium triflates ArN2+ TfO– were obtained easily by diazotization of anilines with tert‐butyl nitrite in the presence of triflic acid. They are highly reactive, forming aromatic iodides, azides, and boronic acids, and also undergo an unusual metal‐free chloro‐dediazonization with chloroform and CCl4.

  在三氟甲磺酸存在下，通过亚硝酸叔丁酯对苯胺进行重氮化，可轻松获得各种稳定，安全且可溶的芳族二氮杂三氟甲磺酸盐ArN 2 +  TfO –。它们具有很高的反应活性，形成芳族碘化物，叠氮化物和硼酸，并且还与氯仿和CCl 4进行了不同寻常的无金属无氯二氮杂脱氮反应。
• Development of a no-carrier-added method for 18F-labelling of aromatic compounds by fluorodediazonation
  作者：Arndt Knöchel、Olaf Zwernemann

  DOI：10.1002/(sici)1099-1344(199604)38:4<325::aid-jlcr843>3.0.co;2-9

  日期：1996.4
• PATRICK, T. B.;WILLAREDT, R. P.;DEGONIA, D. J., J. ORG. CHEM., 1985, 50, N 13, 2232-2235
  作者：PATRICK, T. B.、WILLAREDT, R. P.、DEGONIA, D. J.

  DOI：——

  日期：——
• The sequel to a carbocyclic nucleoside synthesis: a divergent access to both arenediazonium ions and aryl triflates
  作者：C Picherit、F Wagner、D Uguen

  DOI：10.1016/j.tetlet.2004.01.147

  日期：2004.3

  Depending on the amount of acid used, treating aryl-dialkyl triazenes of general structure 3 with triflic acid resulted in the formation of either the corresponding arenediazonium triflates 4 or aryl triflates 8 apparently by two different pathways, the latter conversion being favoured at high acid concentration. (C) 2004 Elsevier Ltd. All rights reserved.