2-Nitro-2'-hydroxy-3',5'-di-tert-butyl-azobenzene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2-Nitro-2'-hydroxy-3',5'-di-tert-butyl-azobenzene
• 英文别名: 2-nitro-2'-hydroxy-3',5'-bis-tert-butylazobenzene；2-Nitro-2'-hydroxy-3',5'-di-tert.-butyl-azobenzene；2-nitro-2'-hydroxy-3',5'-bis-tert.-butylazobenzene；2-nitro-2'-hydroxy-3',5'-di-tert-butylazobenzene；2-nitro-2'-hydroxy-3',5'-di-t-butylazobenzene
• 化学式: C₂₀H₂₅N₃O₃
• 分子量: 355.437
• InChiKey: BBUYLEHVHUQHME-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.09
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-Nitro-2'-hydroxy-3',5'-di-tert-butyl-azobenzene 在 sodium hydroxide 、 锌 作用下， 以 水 为溶剂， 反应 1.0h， 以86%的产率得到紫外线吸收剂UV-320
  参考文献：
  名称：

  锌介导的邻硝基硝基苯偶氮酚在水介质中的还原还原环化反应，不用有机溶剂即可制备2-芳基-2 H-苯并三唑

  摘要：

  锌粉介导的邻硝基硝基偶氮苯酚在碱性溶液中的还原环化，在温和的反应条件下，以高收率提供了相应的2-芳基-2 H-苯并三唑。反应中不使用有机溶剂，并且在后处理中仅使用最小量的有机溶剂。

  DOI：

  10.1002/adsc.200700018
• 作为产物：
  描述：

  2-硝基苯胺 、 2,4-二叔丁基苯酚 、 sodium nitrite 、 盐酸 以75%的产率得到
  参考文献：
  名称：

  ROSEVEAR, J.;WILSHIRE, J. F. K., AUSTRAL. J. CHEM., 1982, 35, N 10, 2089-2093

  摘要：

  DOI：

文献信息

• Process for the production of 2-aryl-2H-benzotriazoles
  申请人：Ciba-Geigy Corporation

  公开号：US04219480A1

  公开（公告）日：1980-08-26

  A process for the production of 2-aryl-2H-benzotriazoles comprises reducing and cyclizing the corresponding o-nitroazobenzenes with hydrogen at a temperature in the range of about 20.degree. C. to about 100.degree. C. and at a pressure in the range of about 15 psia (1 atmosphere) to about 1000 psia (66 atmospheres) in an alkaline medium at a pH over 10 in the presence of a nickel catalyst, preferably molybdenum-promoted Raney nickel. High yields of pure product are obtained directly with a concomitant reduction of undesired by-product and a reduction in effluent pollution problems.

  生产2-芳基-2H-苯并三唑的方法包括在碱性介质中，在pH值大于10的条件下，以镍催化剂为催化剂，优选钼促进的雷尼镍的情况下，通过将相应的邻硝基偶氮苯还原和环化，使温度在大约20°C至大约100°C的范围内，压力在大约15 psia（1大气压）至大约1000 psia（66大气压）的范围内进行。高纯度的产物直接获得，同时伴随着不良副产物的减少以及废水污染问题的减少。
• Process for the preparation of 2-aryl-2H-benzotriazoles
  申请人：Ciba-Geigy Corporation

  公开号：US04220788A1

  公开（公告）日：1980-09-02

  A process for producing benzotriazoles of the formula I ##STR1## wherein R.sub.1 is hydrogen or chlorine, R.sub.2 is hydrogen, chlorine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.9 alkoxycarbonyl, carboxyl or sulfo, R.sub.3 is C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, phenyl, (C.sub.1 -C.sub.8 alkyl)-phenyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.9 alkoxycarbonyl, chlorine, carboxyethyl or C.sub.7 -C.sub.9 phenylalkyl, R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, chlorine or hydroxyl, and R.sub.5 is hydrogen, C.sub.1 -C.sub.12 alkyl, chlorine, C.sub.5 -C.sub.6 cycloalkyl or C.sub.7 -C.sub.9 phenylalkyl, which process comprises treating a benzotriazole-N-oxide of the formula II ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the above meanings, at a temperature of 20.degree.-150.degree. C., with an amine; or treating an o-nitroazobenzene of the formula III ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the above meanings, at a temperature of 20.degree.-150.degree. C., with an amine.

  生产苯并三唑的方法，其中R.sub.1是氢或氯，R.sub.2是氢、氯、C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4烷氧基、C.sub.2 -C.sub.9烷氧羰基、羧基或磺酸基，R.sub.3是C.sub.1 -C.sub.12烷基、C.sub.1 -C.sub.4烷氧基、苯基、(C.sub.1 -C.sub.8烷基)-苯基、C.sub.5 -C.sub.6环烷基、C.sub.2 -C.sub.9烷氧羰基、氯、羧乙基或C.sub.7 -C.sub.9苯基烷基，R.sub.4是氢、C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4烷氧基、氯或羟基，R.sub.5是氢、C.sub.1 -C.sub.12烷基、氯、C.sub.5 -C.sub.6环烷基或C.sub.7 -C.sub.9苯基烷基，该方法包括在20度至150度C的温度下，用胺处理公式II的苯并三唑-N-氧化物；或在20度至150度C的温度下，用胺处理公式III的邻硝基偶氮苯。
• Method of preparing 2-phenyl benzotriazoles
  申请人：Chemipro Kasei Kaisha, Ltd.

  公开号：US05187289A1

  公开（公告）日：1993-02-16

  A method of preparing 2-phenylbenzotriazoles expressed by Formula I: ##STR1## (wherein R.sub.1 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a carboxyl group or a sulfonic acid group; R.sub.2 denotes a hydrogen or chlorine atom, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxyl group having 1 to 4 carbon atoms; R.sub.3 denotes a hydrogen or chlorine atom, an alkyl group having 1 to 12 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted by an alkyl group having 1 to 8 carbon atoms, a phenoxy group or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms; R.sub.4 denotes a hydrogen or chlorine atom, a hydroxyl group or an alkoxyl group having 1 to 4 carbon atoms; and R.sub.5 denotes a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or a phenylalkyl group with an alkyl part having 1 to 4 carbon atoms) comprises reduction with hydrogen of o-nitroazobenzene derivatives expressed by Formula II: ##STR2## (wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 each denote the same as in Formula I), the reduction being effected in a solvent containing water.

  一种制备由式I表示的2-苯基苯并三唑的方法：##STR1##（其中R.sub.1表示氢原子或氯原子，具有1至4个碳原子的较低烷基基团，具有1至4个碳原子的较低烷氧基团，羧基或磺酸基；R.sub.2表示氢原子或氯原子，具有1至4个碳原子的较低烷基基团或具有1至4个碳原子的较低烷氧基团；R.sub.3表示氢原子或氯原子，具有1至12个碳原子的烷基基团，具有1至4个碳原子的较低烷氧基团，苯基，被具有1至8个碳原子的烷基基团替代的苯基，苯氧基或带有1至4个碳原子的烷基部分的苯基烷基基团；R.sub.4表示氢原子或氯原子，羟基或具有1至4个碳原子的烷氧基团；R.sub.5表示氢原子，具有1至12个碳原子的烷基基团或具有1至4个碳原子的烷基部分的苯基烷基基团），包括在含水溶剂中还原由式II表示的o-硝基偶氮苯衍生物：##STR2##（其中R.sub.1，R.sub.2，R.sub.3，R.sub.4和R.sub.5分别与式I中相同），所述还原在含水溶剂中进行。
• Method for preparing 2-phenylbenzotriazoles
  申请人：Chemipro Kasei Kaisha, Ltd.

  公开号：US04943637A1

  公开（公告）日：1990-07-24

  This invention relates to a method for preparing a 2-phenylbenzotriazole of formula I, ##STR1## (wherein R.sub.1 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, a lower alkoxy group having a carbon number of 1 to 4, carboxyl group, or sulfonic acid group; R.sub.2 represents hydrogen or chlorine atom, a lower alkyl group having a carbon number of 1 to 4, or a lower alkoxy group having a carbon number of 1 to 4; R.sub.3 represents hydrogen or chlorine atom, an alkyl group having a carbon number of 1 to 12, a lower alkoxyl group having a carbon number of 1 to 4, phenyl group, a phenyl group substituted with an alkyl group having a carbon number of 1 to 8, phenoxy group, or a phenylalkyl group, the alkyl part of which has a carbon number of 1 to 4; R.sub.4 represents hydrogen or chlorine atom, hydroxyl group, or a lower alkoxy group having a carbon number of 1 to 4; and R.sub.5 represents hydrogen atom, an alkyl group having a carbon number of 1 to 12, or a phenylalkyl group, the alkyl part of which has a carbon number of 1 to 4), which comprises reducing an o-nitroazobenzene of formula III, ##STR2## (wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above) with at least one selected from the group consisting of primary and secondary alcohol reducing agents in the presence of an aromatic ketone catalyst and base. This invention further relates to a method for preparing a 2-phenylbenzotriazole of formula I as defined above, which comprises reducing 1 mole 2-phenylbenzotriazole-N-oxide of formula II, ##STR3## (wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above) with 0.4 to 0.7 mole primary alcohol and/or 0.8 to 1.4 mole secondary alcohol in the presence of an aromatic ketone catalyst and base. This invention still further relates to a method for preparing a 2-phenylbenzotriazole-N-oxide of formula II as defined above, which comprises reducing 1 mole o-nitroazobenzene of formula III as defined above with 0.4 to 0.7 mole primary alcohol and/or 0.8 to 1.4 mole secondary alcohol in the presence of an aromatic ketone catalyst and base.

  这项发明涉及一种制备式I的2-苯基苯并三唑的方法，其中R₁代表氢原子或氯原子，具有1到4个碳原子的低烷基基团，具有1到4个碳原子的低烷氧基团，羧基或磺酸基；R₂代表氢原子或氯原子，具有1到4个碳原子的低烷基基团，或具有1到4个碳原子的低烷氧基团；R₃代表氢原子或氯原子，具有1到12个碳原子的烷基基团，具有1到4个碳原子的低烷氧基团，苯基，带有1到8个碳原子的烷基基团取代的苯基，苯氧基，或苯基烷基基团，其烷基部分具有1到4个碳原子；R₄代表氢原子或氯原子，羟基，或具有1到4个碳原子的低烷氧基团；R₅代表氢原子，具有1到12个碳原子的烷基基团，或苯基烷基基团，其烷基部分具有1到4个碳原子的烷基基团。该方法包括在芳香酮催化剂和碱存在下，用来自主要和次要醇还原剂组成的群体中至少一种，还原式III的o-硝基偶氮苯，其中R₁、R₂、R₃、R₄和R₅如上所定义。这项发明还涉及一种制备上述定义的式I的2-苯基苯并三唑的方法，其中包括在芳香酮催化剂和碱存在下，用0.4到0.7摩尔主要醇和/或0.8到1.4摩尔次要醇还原1摩尔的式II的2-苯基苯并三唑-N-氧化物，其中R₁、R₂、R₃、R₄和R₅如上所定义。这项发明还涉及一种制备上述定义的式II的2-苯基苯并三唑-N-氧化物的方法，其中包括在芳香酮催化剂和碱存在下，用0.4到0.7摩尔主要醇和/或0.8到1.4摩尔次要醇还原1摩尔的式III的o-硝基偶氮苯，如上所定义。
• Novel process for preparation of benzotriazoles using aryldiols and
  申请人：Ciba-Geigy Corporation

  公开号：US04642350A1

  公开（公告）日：1987-02-10

  Process for preparing 2-(2'-hydroxyphenyl)-benzotriazoles of the formula ##STR1## from 2-nitro-2'-hydroxyazobenzenes of the formula ##STR2## which comprises reducing a 2-nitro-2'-hydroxyazobenzene compound in a strongly basic medium in the presence of an aromatic dihydroxy or dioxo compound as catalyst and of an alcohol having more than one carbon atom. The 2-(2'-hydroxyphenyl)-benzotriazole compounds are known stabilizers for organic materials.

  制备公式为##STR1##的2-(2'-羟基苯基)-苯并三唑的过程，包括在强碱性介质中，在芳香族二羟基或二酮化合物的催化下，以及有超过一个碳原子的醇存在的情况下，还原2-硝基-2'-羟基偶氮苯化合物。2-(2'-羟基苯基)-苯并三唑化合物是已知的有机材料稳定剂。