2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide | 94102-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide
• 英文别名: 2-tert-butyl-6-(5-chloro-1-oxidobenzotriazol-1-ium-2-yl)-4-methylphenol
• CAS: 94102-12-2
• 化学式: C₁₇H₁₈ClN₃O₂
• 分子量: 331.802
• InChiKey: OCTVZYZBPDCPIE-UHFFFAOYSA-N

物化性质

• 沸点：
  494.2±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide 、 9-芴酮 在 sodium hydroxide 、 paraformaldehyde 作用下， 以 甲醇 、 水 为溶剂， 生成 紫外线吸收剂 UV-326
  参考文献：
  名称：

  Method for preparing 2-phenylbenzotriazoles and

  摘要：

  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R.sub.1代表氢原子或氯原子，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，或磺酸基团；R.sub.2代表氢原子或氯原子，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代表氢原子或氯原子，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，一个用具有1至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至4个碳原子；R.sub.4代表氢原子或氯原子，羟基，或具有1至4个碳原子的较低烷氧基团；R.sub.5代表氢原子，具有1至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至4个碳原子。该方法包括在芳香酮催化剂和碱的存在下，用醛还原剂还原式III的邻硝基偶氮苯，其中R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5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，包括在芳香酮催化剂和碱的存在下，用1至4摩尔醛还原1摩尔的式II的2-苯基苯并三唑-N-氧化物，其中R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5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，包括在芳香酮催化剂和碱的存在下，用1至2摩尔醛还原1摩尔的上述定义的式III的邻硝基偶氮苯。

  公开号：

  US04780541A1
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 2-Nitro-4-chloro-2'-hydroxy-3'-tert-butyl-5'-methyl-azobenzene 、 葡萄糖 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide
  参考文献：
  名称：

  Method for preparing 2-phenylbenzotriazoles and

  摘要：

  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##

  公开号：

  US04835284A1

文献信息

• METHOD FOR PREPARING 2-(2-HYRDROXYPHENYL)-2H-BENZOTRIAZOLE
  申请人：——

  公开号：US20030050480A1

  公开（公告）日：2003-03-13

  This invention provides a method for preparing 2-(2-hydroxyphenyl)-2H-benzotriazole of formula (I) below, consisting of steps of a) performing a first reduction in which hydrazine hydrate is added to a compound of formula (II) below with or without a phase transition catalyst in the presence of solvents which include a nonpolar solvent, water, and an alkaline compound, thereby preparing a compound of formula (III) below, and b) performing a second reduction in which water is added to the compound of formula (III) prepared in step a), and then zinc powder and sulfuric acid are added thereto with or without the phase transition catalyst, wherein, X is halogen or hydrogen, R is hydrogen, C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl, phenyl, or phenyl-C 1 -C 4 alkyl; and R′ is C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl, phenyl, or phenyl-C1-C4 alkyl 1

  本发明提供了一种制备式（I）下的2-（2-羟基苯基）-2H-苯并三唑的方法，包括以下步骤：a）在非极性溶剂、水和碱性化合物的存在下，在化合物式（II）下添加肼水合物进行第一次还原，有或没有相转移催化剂，从而制备式（III）下的化合物；b）在步骤a）中制备的式（III）下的化合物中加入水，然后加入锌粉和硫酸，有或没有相转移催化剂，其中，X是卤素或氢，R是氢、C1-C12烷基、C5-C8环烷基、苯基或苯基-C1-C4烷基；R'是C1-C12烷基、C5-C8环烷基、苯基或苯基-C1-C4烷基。
• 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.

  本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至4个碳原子的低级烷基基团、具有1至4个碳原子的低级烷氧基团、羧基团或磺酸基团；R2代表氢原子或氯原子，具有1至4个碳原子的低级烷基基团或具有1至4个碳原子的低级烷氧基团；R3代表氢原子或氯原子、具有1至12个碳原子的烷基基团、具有1至4个碳原子的低级烷氧基团、苯基、被具有1至8个碳原子的烷基基团取代的苯基、苯氧基或苯基烷基，其中烷基部分具有1至4个碳原子；R4代表氢原子或氯原子、羟基或具有1至4个碳原子的低级烷氧基团；R5代表氢原子、具有1至12个碳原子的烷基基团或苯基烷基，其中烷基部分具有1至4个碳原子。该方法包括在芳香酮催化剂和碱的存在下，使用一种或多种选择自原醇还原剂和二级醇还原剂的还原剂，还原式III的o-硝基偶氮苯，其中：R1、R2、R3、R4和R5如上所定义。本发明还涉及一种制备如上定义的式I的2-苯基苯并三唑的方法，该方法包括在芳香酮催化剂和碱的存在下，使用0.4至0.7摩尔的原醇和/或0.8至1.4摩尔的二级醇，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。本发明还进一步涉及一种制备如上定义的式II的2-苯基苯并三唑-N-氧化物的方法，该方法包括在芳香酮催化剂和碱的存在下，使用0.4至0.7摩尔的原醇和/或0.8至1.4摩尔的二级醇，还原如上定义的式III的o-硝基偶氮苯1摩尔。
• 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.

  本发明提供了一种制备2-芳基-2H-苯并三唑的方法，通过在存在芴酚催化剂和碱的溶液中，使用具有醛基的糖类还原剂还原o-硝基偶氮苯。反应温度在约60℃至约80℃之间。相比使用芳香酮催化剂，反应时间和催化剂用量显著降低。本发明还提供了一种方法，通过在类似条件下，在存在芴酚的情况下，使用具有醛基的糖类还原剂还原2-芳基-2H-苯并三唑-N-氧化物中间体来制备2-芳基-2H-苯并三唑。
• Method of preparing 2-phenyl benezothriazoles
  申请人：Chemipro Kasei Kaisha, Ltd.

  公开号：US05104992A1

  公开（公告）日：1992-04-14

  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 alkoxy 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 reducing with hydrogen 2-phenylbenzotriazole-N-oxides expressed by Formula II: ##STR2## (wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 each denotes the same as in Formula I).

  一种制备式I所示的2-苯基苯并三氮唑的方法：##STR1##（其中R.sub.1表示氢或氯原子，具有1至4个碳原子的低烷基，具有1至4个碳原子的低烷氧基，羧基或磺酸基；R.sub.2表示氢或氯原子，具有1至4个碳原子的低烷基或具有1至4个碳原子的低烷氧基；R.sub.3表示氢或氯原子，具有1至12个碳原子的烷基，具有1至4个碳原子的低烷氧基，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）包括将式II所示的2-苯基苯并三氮唑-N-氧化物还原为：##STR2##（其中R.sub.1，R.sub.2，R.sub.3，R.sub.4和R.sub.5与式I中的相同）。
• 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)。