2-Brom-6-chlormethyl-4-nitrophenol | 10491-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-Brom-6-chlormethyl-4-nitrophenol
• 英文别名: 2-bromo-6-chloromethyl-4-nitrophenol；2-Brom-4-nitro-6-chlormethylphenol；2-Bromo-6-(chloromethyl)-4-nitrophenol；2-bromo-6-(chloromethyl)-4-nitrophenol
• CAS: 10491-25-5
• 化学式: C₇H₅BrClNO₃
• 分子量: 266.479
• InChiKey: RCZROJNOIDXUPX-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  375.9±42.0 °C(Predicted)
• 密度：
  1.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Brom-6-chlormethyl-4-nitrophenol 在 四(三苯基膦)钯 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 4-(4-methoxyphenyl)-5a,6,6,8-tetramethyl-2-nitro-12H-indolo[2,1-b][1,3]benzoxazine
  参考文献：
  名称：

  Improving the photochromic properties of indolo[2,1-b][1,3]benzoxazines with phenylic substituents

  摘要：

  This work presents a series of new photochromic compounds of indolo[2,1-b][1,3]benzoxazine family. Photochromic systems based on the opening and closing of [1,3]oxazine ring are among the fastest photochromic switches, completing the full "on-off" cycle in less than few tens of nanoseconds. Furthermore, indolo[2,1-b][1,3]benzoxazines are distinguished for their excellent fatigue resistance as well as substantial quantum yield of photochromic transformation, both important for practical applications. Photochromic properties can be selectively altered by introducing structural modifications to the parent compound, namely, by varying substituents attached to certain positions. We aimed to enhance the photochromic performance of indolo[2,1-b1[1,31benzoxazines by modifying the parent molecule with phenylic substituents. In this article we introduce 10 new compounds, which are classified into two groups according to the attachment site of the phenylic substituent: group I compounds have modifications in the 5th position of the indole ring, group II-in the 4th position of the indolo[2,1-b][1,3]benzoxazine molecule. The investigation of photochromic properties of the compounds in acetonitrile solutions revealed the outstanding parameters of the new molecules. Group I compounds have an exceptional feature in the induced absorption spectra - an additional band in the nIR, which is observed for the first time in the compounds of indolo[2,1-b][1,3]benzoxazine family. On the other hand, all group II compounds display enhanced switching speeds; indeed, the fastest relaxation time value ever reported for similar compounds was measured in this group. In general, group I compounds were found to be superior to both parent molecule and group II compounds in both photostability and quantum yield, thus demonstrating the potential of molecular design for development and realization of photochromic compounds with desired properties. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.12.022
• 作为产物：
  描述：

  2-溴-4-硝基苯酚 、 氯甲基甲基醚 在 zinc(II) chloride 作用下， 反应 36.0h， 以12%的产率得到2-Brom-6-chlormethyl-4-nitrophenol
  参考文献：
  名称：

  Stein, Guenter; Boehmer, Volker; Lotz, Werner, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1981, vol. 36, # 2, p. 231 - 241

  摘要：

  DOI：

文献信息

• Kinetics of the reaction of chloromethylated phenols with aniline and substituted anilines
  作者：Günter Stein、Hermann Kämmerer、Volker Böhmer

  DOI：10.1039/p29840001285

  日期：——

  The kinetics of the reaction of several chloromethylated phenols with substituted anilines, mainly p-nitroaniline, were studied for dimethyl sulphoxide solution by conductivity measurements. Substitution of the chlorine atoms proceeds in two steps. In a reversible step hydrogen chloride is eliminated by a suitable base to form a quinone methide. The aniline is added to this intermediate in the second

  通过电导率测量研究了几种氯甲基化酚与取代苯胺（主要是对硝基苯胺）的反应动力学。氯原子的取代分两个步骤进行。在可逆步骤中，氯化氢被合适的碱除去，从而形成醌甲基化物。在第二步中将苯胺添加到该中间体中，形成苯胺基甲基苯酚作为产物。如果使用弱碱性苯胺（例如对硝基苯胺），第一步中的碱可以是溶剂，如果使用更多碱性苯胺（例如苯胺本身）进行反应，则苯胺可以是苯胺。
• Stein, Guenter; Boehmer, Volker; Lotz, Werner, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1981, vol. 36, # 2, p. 231 - 241
  作者：Stein, Guenter、Boehmer, Volker、Lotz, Werner、Kaemmerer, Hermann

  DOI：——

  日期：——
• Improving the photochromic properties of indolo[2,1-b][1,3]benzoxazines with phenylic substituents
  作者：Vladislava Voiciuk、Kipras Redeckas、Vytas Martynaitis、Rasa Steponavičiūtė、Algirdas Šačkus、Mikas Vengris

  DOI：10.1016/j.jphotochem.2013.12.022

  日期：2014.3

  This work presents a series of new photochromic compounds of indolo[2,1-b][1,3]benzoxazine family. Photochromic systems based on the opening and closing of [1,3]oxazine ring are among the fastest photochromic switches, completing the full "on-off" cycle in less than few tens of nanoseconds. Furthermore, indolo[2,1-b][1,3]benzoxazines are distinguished for their excellent fatigue resistance as well as substantial quantum yield of photochromic transformation, both important for practical applications. Photochromic properties can be selectively altered by introducing structural modifications to the parent compound, namely, by varying substituents attached to certain positions. We aimed to enhance the photochromic performance of indolo[2,1-b1[1,31benzoxazines by modifying the parent molecule with phenylic substituents. In this article we introduce 10 new compounds, which are classified into two groups according to the attachment site of the phenylic substituent: group I compounds have modifications in the 5th position of the indole ring, group II-in the 4th position of the indolo[2,1-b][1,3]benzoxazine molecule. The investigation of photochromic properties of the compounds in acetonitrile solutions revealed the outstanding parameters of the new molecules. Group I compounds have an exceptional feature in the induced absorption spectra - an additional band in the nIR, which is observed for the first time in the compounds of indolo[2,1-b][1,3]benzoxazine family. On the other hand, all group II compounds display enhanced switching speeds; indeed, the fastest relaxation time value ever reported for similar compounds was measured in this group. In general, group I compounds were found to be superior to both parent molecule and group II compounds in both photostability and quantum yield, thus demonstrating the potential of molecular design for development and realization of photochromic compounds with desired properties. (C) 2014 Elsevier B.V. All rights reserved.