2-Nitro-4-chloro-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-4-chloro-2'-hydroxy-3',5'-di-tert-butyl-azobenzene
• 英文别名: 2-(4'-chloro-2'-nitrophenylazo)-4,6-di-tert-butylphenol；2-Nitro-4-chloro-2'-hydroxy-3',5'-di-tert.-butyl-azobenzene；2-nitro-4-chloro-2'-hydroxy-3',5'-ditert.-butylazobenzene；2,4-di-tert-butyl-6-(4-chloro-2-nitro-phenylazo)-phenol；2-nitro-4-chloro-2'-hydroxy-3',5'-di-t-butylazobenzene
• 化学式: C₂₀H₂₄ClN₃O₃
• 分子量: 389.882
• InChiKey: IIHNCIPIAMRRIQ-GHVJWSGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  27.0
• 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-4-chloro-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90%的产率得到紫外线吸收剂 UV-327
  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：

  4-氯-2-硝基苯胺 、 2,4-二叔丁基苯酚 、 sodium nitrite 、 盐酸 以55%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 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。
• Processes for the preparation of benzotriazole UV absorbers
  申请人：——

  公开号：US20020035175A1

  公开（公告）日：2002-03-21

  Provided is a process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzo ring, for example a trifluoromethyl group, which involves diazotizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means. Also provided is a novel one-pot, multiphase reaction for the preparation of 2(2-nitrophenylazo) substituted phenols, which are precursors for 2H-benzotriazole UV absorbers.

  提供了一种制备在苯环的5位含有全氟烷基基团（例如三氟甲基基团）的2H-苯并三唑紫外吸收剂的方法，该方法涉及使用浓硫酸加硝酸钠或亚硝基硫酸制备全氟烷基取代的邻硝基苯胺，以形成相应的单氮偶联苯中间体，通过传统还原手段将二氮盐中间体还原为相应的5-全氟烷基取代的2H-苯并三唑紫外吸收剂化合物。还提供了一种用于制备2(2-硝基苯基偶氮)取代酚的新型一锅多相反应，这些化合物是2H-苯并三唑紫外吸收剂的前体。
• 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。
• Process for the manufacture of 2-(2-hydroxyphenyl)benztriazoles
  申请人：Ciba-Geigy Corporation

  公开号：US04001266A1

  公开（公告）日：1977-01-04

  Process for the manufacture of 2-(2-hydroxyphenyl)benztriazoles of the formula I ##STR1## wherein R.sub.1 denotes hydrogen or halogen, R.sub.2 denotes hydrogen, alkyl, alkoxy, alkylsulphonyl, acylamino, --SO.sub.3 H, --COOH or halogen, R.sub.3 denotes hydrogen, alkyl, cycloalkyl, aralkyl, aryl or halogen, R.sub.4 denotes hydrogen, alkyl, alkoxy or --OH and R.sub.5 denotes hydrogen, alkyl, cycloalkyl, aralkyl, aryl, carboxyalkyl, alkoxy, acylamino or halogen, characterized in that a 2-(2-hydroxyphenyl)-benztriazole-1 oxide in the formula III ##STR2## is reacted with 0.5 to 0.6 mol equivalent of hydrazine hydrate at a temperature above 100.degree. C, in a high-boiling ether as the solvent and in the presence of a base.

  制备公式I的2-(2-羟基苯基)苯并三唑的方法，其中R.sub.1代表氢或卤素，R.sub.2代表氢、烷基、烷氧基、烷基磺酰基、酰胺基、--SO.sub.3 H、--COOH或卤素，R.sub.3代表氢、烷基、环烷基、芳基烷基、芳基或卤素，R.sub.4代表氢、烷基、烷氧基或--OH，R.sub.5代表氢、烷基、环烷基、芳基烷基、芳基、羧基烷基、烷氧基、酰胺基或卤素，其特征在于在公式III中的2-(2-羟基苯基)-苯并三唑-1氧化物与0.5至0.6摩尔当量的水合肼在高于100摄氏度的温度下，在高沸点醚作为溶剂并在碱的存在下反应。
• A method for producing A 2-phenylbenzotriazole
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0160246A1

  公开（公告）日：1985-11-06

  A method for producing a 2-phenylbenzotriazole useful as an ultraviolet absorber and represented by the general formula (III), wherein R1 represents a hydrogen or chlorine atom, or a C1-C4 lower alkyl or lower alkoxy, carboxy or sulfonic acid group, R2 represents a hydrogen or chlorine atom, or a C1-C4 lower alkyl or lower alkoxy group, and R3, R4 and R5 each represent a hydrogen or chlorine atom, or a C1-C12 alkyl, phenyl, C1-C8 alkyl group-substituted phenyl, phenyl-C1-C8 alkyl, hydroxy, phenoxy or C1-C4 alkoxy group, which comprises reducing a 2-phenylbenzotriazol-N-oxide represented by the general formula (II), wherein RI, R2, R3, R4 and R5 represent the same meanings as described above, with one or more members selected from the group consisting of phosphorus, hypophosphorous acid and its salts in the presence of an alkali and a napthoquinone in the absence or presence of a surface active agent, or comprises reducing an o-nitroazobenzene represented by the general formula (I), wherein R1, R2, R3, R4 and R5 represent the same meanings as described above, with one or more members selected from the group consisting of phosphorus, hypophosphorous acid and its salts in the presence of an alkali and a naphthoquinone in the absence or presence of a surface active agent to obtain a 2-phenylbenzotriazol-N-oxide represented by the general formula (II), wherein R1, R2, R3, R4 and R5 represent the same meanings as describe above, and reducing the resulting compound (II) with one or more members selected from the group consisting of phosphorus, hypophosphorous add and its salts in the presence of an alkali and a naphthoquinone in the absence or presence of a surface active agent.

  一种由通式(III)表示的可用作紫外线吸收剂的2-苯基苯并三唑的生产方法、 其中 R1 代表氢原子或氯原子，或 C1-C4 低级烷基或低级烷氧基、羧基或磺酸基，R2 代表氢原子或氯原子，或 C1-C4 低级烷基或低级烷氧基，R3、R4 和 R5 各代表氢原子或氯原子，或 C1-C12 烷基、苯基、C1-C8 烷基取代的苯基、苯基-C1-C8 烷基、羟基、苯氧基或 C1-C4 烷氧基，该方法包括还原通式（II）代表的 2-苯基苯并三唑-N-氧化物、 其中 RI、R2、R3、R4 和 R5 代表与上述相同的含义，一个或多个成员选自磷、次磷 酸及其盐组成的组，在碱和萘醌存在或不存在表面活性剂的情况下，或包括还原通式 （I）所代表的邻硝基偶氮苯、 其中 R1、R2、R3、R4 和 R5 代表与上述相同的含义，在无表面活性剂或有表面活性剂存在的情况下，用选自磷、次磷酸及其盐组成的组中的一个或多个成员，在碱和萘醌存在的情况下，得到通式 (II) 所代表的 2-苯基苯并三唑-N-氧化物、 其中 R1、R2、R3、R4 和 R5 所代表的含义与上述相同，在没有或有表面活性 剂存在的情况下，在碱和萘醌存在的情况下，用选自磷、次磷加及其盐组成的 组中的一个或多个成员还原所得到的化合物 (II)。