2-(4'-hydroxyphenylazo)-6-nitrobenzothiazole | 65902-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(4'-hydroxyphenylazo)-6-nitrobenzothiazole
• 英文别名: 4-(6-nitrobenzothiazole-2-ylazo)phenol；4-(6-nitrobenzothiazol-2-ylazo)phenol；4-[2-(6-Nitro-1,3-benzothiazol-2-yl)hydrazinylidene]cyclohexa-2,5-dien-1-one；4-[(6-nitro-1,3-benzothiazol-2-yl)diazenyl]phenol
• CAS: 65902-49-0
• 化学式: C₁₃H₈N₄O₃S
• 分子量: 300.298
• InChiKey: UNPSOEPILYXCQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4'-hydroxyphenylazo)-6-nitrobenzothiazole 、 4-decyloxybenzoyl chloride 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Mesogenic Benzothiazole Derivatives with a Polar Nitro Substituent

  摘要：

  Two new mesogenic homologous series containing 6-nitrobenzothiazole moiety at the terminus of the molecule, viz 2-(4'-n-alkoxyphenylazo)-6-nitrobenzothiazoles and 2-[4'-(4 ''-n alkoxybenzoyloxy)phenylazo]-6-nitrobenzothiazoles were synthesized. The molecular structures of these new compounds of both the series have been characterized by elemental analysis, FTIR, and NMR spectral studies. The mesomorphic behavior has been studied using mainly polarized microscopy and in some cases differential scanning calorimetry as well. All the nine compounds of the series I are mesogenic and exhibit only the smectic A mesophase. In series II, all the twelve members synthesized exhibit enantiotropic mesomorphism. This series exhibits enantiotropic nematic mesophase from methoxy to n-heptyloxy derivatives. The smectic C mesophase commences from methoxy derivative, and persist up to n-butyloxy derivative, whereas the smectic A mesophase enters from the n-butyloxy derivative, and remains up to the last member synthesized. The mesomorphic properties of the present series are compared with other structurally related series to evaluate the effect of the benzothiazole ring and the polar nitro substituent on mesomorphism.

  DOI：

  10.1080/15421400802697616
• 作为产物：
  描述：

  2-氨基-6-硝基苯并噻唑 、 苯酚 在 硫酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.33h， 以50%的产率得到2-(4'-hydroxyphenylazo)-6-nitrobenzothiazole
  参考文献：
  名称：

  Polyamidoimides with side chromophoric groups

  摘要：

  通过将含有侧羧基的聚酰胺酰亚胺与染料缩水甘油醚、4-(4-硝基苯偶氮)苯酚和 4-(6-硝基苯并噻唑-2-基)苯酚酯化，详细阐述了将发色团引入聚合物侧链的新方法。找到的最佳改性条件可以使 15%、30%、50% 和 90% 的羧基酯化。根据酯化程度的不同，合成的聚合物具有重要的物理机械性能（E = 2.8-3.3 GPa，σu = 69-90 MPa，εu = 38-77%），玻璃化温度为 115-125 ℃。在电晕放电中进行发色团定向后，所有聚合物都显示出二阶非线性光学特性。

  DOI：

  10.1007/s11172-005-0431-0

文献信息

• Series of Azobenzothiazole-Based Initiators for Atom Transfer Radical Polymerization of Methyl Methacrylate
  作者：Mengjun Jiang、Gangming Cai、Yaoyuan Zhou、Xiaobo Gu、Rongjun Zhang

  DOI：10.14233/ajchem.2013.15006

  日期：——

  2-Bromo-2-methyl-propionic acid 4-benzothiazole-2-ylazo-phenyl ester (BPBE), 2-bromo-2-methyl-propionic acid 4-(6-methoxy-benzothiazole-2-ylazo)phenyl ester (BPMBE) and 2-bromo-2-methyl-propionic acid 4-(6-nitro-benzothiazole-2-ylazo)phenyl ester (BPNBE) were synthesized and acted as initiators for the heterogeneous atom transfer radical polymerization of methyl methacrylate under copper(I) bromide/2,2-bipyridine catalytic system, respectively. The azobenzothiazole-based end group of polymethyl methacrylate was characterized via UV-visible spectroscopy. All rates of polymerizations exhibited first-order kinetic with respect to the monomer and a linear increase in the number-average molecular weight with increasing monomer conversion was observed for all these initiation systems. The polydispersity indices of the polymethyl methacrylates were relatively low (1.08-1.37) up to high conversions at 60 ºC. Moreover, the initiation systems exhibit a high activity that polymerizations could even be performed at ambient temperature (30 ºC).

  2-Bromo-2-methyl-propionic acid 4-benzothiazole-2-ylazo-phenyl ester (BPBE)、合成了 2-溴-2-甲基丙酸 4-(6-甲氧基-苯并噻唑-2-基偶氮)苯基酯（BPMBE）和 2-溴-2-甲基丙酸 4-(6-硝基-苯并噻唑-2-基偶氮)苯基酯（BPNBE），并在溴化铜（I）/2,2-联吡啶催化体系下分别用作甲基丙烯酸甲酯异相原子转移自由基聚合的引发剂。聚甲基丙烯酸甲酯的偶氮苯并噻唑基端基通过紫外可见光谱进行了表征。在所有这些引发体系中，所有聚合速率都表现出与单体有关的一阶动力学，并且随着单体转化率的增加，平均分子量呈线性增加。聚甲基丙烯酸甲酯的多分散指数相对较低（1.08-1.37），直到 60 ºC 时的高转化率。此外，这些引发体系表现出很高的活性，甚至可以在环境温度（30 ºC）下进行聚合。