4-甲基-2-(1-氧代-2H-苯并三唑-2-基)-苯酚 | 54659-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-甲基-2-(1-氧代-2H-苯并三唑-2-基)-苯酚
• 英文名称: 2-(2'-hydroxy-5'-methylphenyl)benzotriazole N-oxide
• 英文别名: 2-(2-hydroxy-5-methylphenyl)benztriazole N-oxide；4-methyl-2-(1-oxidobenzotriazol-1-ium-2-yl)phenol
• CAS: 54659-85-7
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: YGAXMRPKYHKRBK-UHFFFAOYSA-N

物化性质

• 熔点：
  142-143 °C(Solv: ethanol (64-17-5))
• 沸点：
  467.2±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲基-2-(1-氧代-2H-苯并三唑-2-基)-苯酚 在 aluminum nickel 二甲胺 作用下， 以55%的产率得到紫外线吸收剂 UV-P
  参考文献：
  名称：

  Method of preparing 2-phenyl benezothriazoles

  摘要：

  一种制备由式I表示的2-苯基苯并三氮唑的方法：##STR1##（其中R.sub.1表示氢原子或氯原子，具有1至4个碳原子的低碳链基，具有1至4个碳原子的低碳氧基，羧基或磺酸基；R.sub.2表示氢原子或氯原子，具有1至4个碳原子的低碳链基或具有1至4个碳原子的低碳氧基；R.sub.3表示氢原子或氯原子，具有1至12个碳原子的烷基，具有1至4个碳原子的低碳氧基，苯基，被具有1至8个碳原子的烷基取代的苯基，苯氧基或具有1至4个碳原子的烷基部分的苯基烷基；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；R.sub.5表示氢原子，具有1至12个碳原子的烷基或具有1至4个碳原子的烷基部分的苯基烷基）包括用氢还原由式II表示的2-苯基苯并三氮唑-N-氧化物：##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）。

  公开号：

  US05104992A1
• 作为产物：
  描述：

  2-(2’-硝基苯偶氮)-4-甲基酚 在 sodium hydroxide 、 苯甲醇 作用下， 反应 1.5h， 以90%的产率得到4-甲基-2-(1-氧代-2H-苯并三唑-2-基)-苯酚
  参考文献：
  名称：

  One-Pot Synthesis of Benzotriazoles and Benzotriazole 1-Oxides by Reductive Cyclization of o-Nitrophenylazo Compounds with Benzyl Alcohol

  摘要：

  Reductive cyclization of 2-[(nitrophenyl)azophenols 1 with benzyl alcohol and sodium hydroxide afforded 2-(2H-benzotriazol-2-yl)phenols 3 and their 1-oxide 2 in good to excellent yields.

  DOI：

  10.3987/com-09-11759

文献信息

• Method for preparing 2-phenylbenzotriazoles and
  申请人：Chemipro Kasei Kaisha, Ltd.

  公开号：US04835284A1

  公开（公告）日：1989-05-30

  This invention relates to a method for preparing 2-phenylbenzotriazoles having the formula I, ##STR1##

  这项发明涉及一种制备具有化学式I的2-苯基苯并三唑的方法，##STR1##
• 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。
• Fluorenol catalyzed reduction of o-nitroazobenzenes and
  申请人：Fairmont Chemical Company, Inc.

  公开号：US05262541A1

  公开（公告）日：1993-11-16

  A process for producing 2-aryl-2H-benzotriazole by reducing an o-nitroazobenzene with a saccharide having an aldehyde group as a reducing agent in the presence of fluorenol as a catalyst and a base in solution. The reaction is conducted at a temperature of from about 60.degree. C. to about 80.degree. C. The reaction time and amount of catalyst is significantly reduced compared to the use of an aromatic ketone catalyst. The invention also provides a method for producing 2-aryl-2H-benzotriazole by reducing a 2-aryl-2H-benzotriazole-N-oxide intermediate with a saccharide having an aldehyde group as a reducing agent, in the presence of fluorenol under similar conditions.

  一种通过在溶液中使用氟诺酚作为催化剂和碱，以含有醛基的糖类作为还原剂还原邻硝基偶氮苯制备2-芳基-2H-苯并三唑的方法。反应在约60°C至约80°C的温度下进行。与使用芳香酮催化剂相比，反应时间和催化剂用量显著减少。该发明还提供了一种通过在类似条件下在氟诺酚存在下使用含有醛基的糖类作为还原剂还原2-芳基-2H-苯并三唑-N-氧化物中间体的方法，制备2-芳基-2H-苯并三唑的方法。
• 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。
• Method of making hydroxyarylbenzotriazoles and their N-oxides
  申请人：Uniroyal Inc.

  公开号：US03978074A1

  公开（公告）日：1976-08-31

  Catalytic hydrogenation of o-nitrophenylazohydroxyaryls in an alkaline medium yields hydroxyarylbenzotriazoles; under mild conditions an N-oxide is formed. E.g., 6-tert-butyl-2-(5'-chloro-2'-nitrohenylazo)-p-cresol is hydrogenated to 5-chloro-2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)benzotriazole, using platinum sulfide catalyst in the presence of sodium hydroxide: ##SPC1## In this case A in the starting chemical is 5-chloro, n is 1, Ar is phenyl nucleus, m is 2, one B is 6-tert-butyl and the other B is 4-methyl; in the product x is zero. Chemicals useful for various purposes, including the stabilization of polymeric materials (e.g., polypropylene, polyvinyl chloride) against light, may be made by the process.

  在碱性介质中，对-硝基苯基偶氮羟基芳基的催化氢化产生羟基芳基苯并三唑；在温和条件下形成N-氧化物。例如，6-叔丁基-2-(5'-氯-2'-硝基苯基偶氮)-对甲酚在铂砷化物催化剂存在下与氢氧化钠反应，被氢化为5-氯-2-(3'-叔丁基-2'-羟基-5'-甲基苯基)苯并三唑。在这种情况下，起始化学物质中的A是5-氯，n为1，Ar是苯核，m为2，一个B是6-叔丁基，另一个B是4-甲基；在产物中x为零。该过程可制备用于各种目的的化学品，包括用于稳定聚合物材料（例如聚丙烯、聚氯乙烯）抵抗光照的化学品。