4-chloro-1,2-bis(trifluoromethyl)benzene | 320-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-1,2-bis(trifluoromethyl)benzene
• 英文别名: 4-Chloro-1,2-bis-(trifluoromethyl)benzene
• CAS: 320-30-9
• 化学式: C₈H₃ClF₆
• 分子量: 248.555
• InChiKey: PWDDGDIIBURINF-UHFFFAOYSA-N

物化性质

• 沸点：
  157-160 °C
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3,4-bis(benzyloxy)-6-ethenylpyridazine 、 4-chloro-1,2-bis(trifluoromethyl)benzene 在 双(三环己基膦)二氯化钯 、 palladium on activated charcoal 、 氢气 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 6-{2-[3,4-bis(trifluoromethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3-one
  参考文献：
  名称：

  NOVEL COMPOUNDS

  摘要：

  本发明提供了式（I）的化合物及其药用盐，其中R1和R2如规范中定义，以及它们的制备方法、含有它们的药物组合物以及它们在治疗中的用途。

  公开号：

  US20130052281A1
• 作为产物：
  描述：

  1,2-双(三氟甲基)苯 在 氯 、 三氯化铁 、 甲烷 作用下， 生成 4-chloro-1,2-bis(trifluoromethyl)benzene
  参考文献：
  名称：

  Chlorination of (perfluoroalkyl) benzenes

  摘要：

  公开号：

  US02601310A1

文献信息

• [EN] PYRIDAZINONE COMPOUNDS AND THEIR USE AS DAAO INHIBITORS<br/>[FR] COMPOSÉS DE PYRIDAZINONE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA DAAO
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2013027000A1

  公开（公告）日：2013-02-28

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1 and R2 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了式（I）的化合物及其药用盐，其中R1和R2如规范中定义，其制备方法，含有它们的药物组合物以及它们在治疗中的用途。
• Iron-Catalyzed Isopropylation of Electron-Deficient Aryl and Heteroaryl Chlorides
  作者：James N. Sanderson、Andrew P. Dominey、Jonathan M. Percy

  DOI：10.1002/adsc.201601097

  日期：2017.3.20

  of secondary alkyl‐substituted aryl and heteroaryl chlorides challenge both selectivity and functional group tolerance. This contribution describes the use of statistical design of experiments to develop an effective procedure for the preparation of isopropyl‐substituted (hetero)arenes with minimal isopropyl to n‐propyl isomerization. The reaction tolerates electronically diverse aryl chloride coupling

  传统的制备仲烷基取代的芳基和杂芳基氯化物的方法对选择性和官能团耐受性都提出了挑战。这种贡献描述了使用的实验统计设计来开发用于制备异丙基取代的（杂）芳烃的具有最小异丙到一个有效的过程Ñ丙基异构化。该反应可耐受电子形式多样的芳基氯偶合体，对于电子含量极低的芳族环（如酯和酰胺），可观察到出色的转化率。发现富电子体系，包括甲基和甲氧基取代的芳基氯，反应性较低。此外，当杂芳基氯化物进入交叉偶联方案时，发现该反应是最成功的。通过映射取代基对反应选择性的影响，我们能够证明缺电子的芳基氯对于有效偶联是必不可少的，并使用电子结构计算通过估计每种芳基氯的电子亲和力来预测成功偶联的可能性。使用选定的芳基氯化物可达到中等程度的分离收率，对于所有偶合的杂芳基氯化物，获得中等至良好的分离产率。当使用2,6-二氯喹啉时，观察到极好的选择性，可在具有挑战性的底物上单取代。
• Benzene derivatives containing halogenated methyl groups and process of preparing them
  申请人：GEN ANILINE WORKS INC

  公开号：US02121330A1

  公开（公告）日：1938-06-21

  A benzene derivative containing at least two methyl groups and having two methyl groups in o-position is chlorinated so as to exchange five hydrogen atoms of the two o-methyl groups for chlorine, the chlorine is exchanged for fluorine, and the product again chlorinated to give an o-trifluoromethyl-difluorochloromethylbenzene, in which the chlorine may be again replaced by fluorine to give an o-dimethylbenzene hexafluoride. The products are intermediates for dyestuffs, fungicides, and insecticides. In examples: (1) o-xylene or 4-chloro-o-xylene or a dichloro-o-xylene is pentachlorinated, for example, according to the process described in Specification 464,859, the chlorine exchanged for fluorine, and the product again chlorinated to give 1-trifluoromethyl-2-difluorochloromethylbenzene or its 4-chlor or dichlor derivatives, which are then converted to the corresponding hexafluorides; (2) pseudocumene, or a chloro or dichloro derivative, is octachlorinated, the chlorine replaced by fluorine and the product again chlorinated to give a bis-trifluoromethyldifluorochloromethylbenzene, which is then converted to the corresponding nonofluoride; (3) durene is converted by way of its decachloride and decafluoride to a bis-trifluoromethyl-bis-difluorochloromethylbenzene, and thence to durene dodecafluoride. Specification 395,227 also is referred to.

  一种苯衍生物，含有至少两个甲基基团，并且在o-位置有两个甲基基团，经氯化后，将这两个o-甲基基团的五个氢原子交换为氯原子，然后再将氯原子交换为氟原子，再次氯化得到一种o-三氟甲基-二氟氯甲基苯，其中氯原子可以再次被氟原子取代，得到一种o-二甲基苯六氟化物。这些产物是染料、杀菌剂和杀虫剂的中间体。在示例中：(1) o-二甲苯或4-氯-o-二甲苯或二氯-o-二甲苯进行五氯化，例如，根据规范464,859中描述的过程，将氯原子交换为氟原子，然后再次氯化得到1-三氟甲基-2-二氟氯甲基苯或其4-氯或二氯衍生物，然后转化为相应的六氟化物；(2) 假山梅烷或氯或二氯衍生物进行八氯化，将氯原子替换为氟原子，然后再次氯化得到双-三氟甲基二氟氯甲基苯，然后转化为相应的九氟化物；(3) 二甲苯通过其十氯化物和十氟化物转化为双-三氟甲基-双-二氟氯甲基苯，然后转化为二甲苯十二氟化物。还参考规范395,227。
• Cyanation of haloaromatics utilizing catalysts generated in situ starting with NiCl2 or NiCl2 6H2O
  申请人：OCCIDENTAL CHEMICAL CORPORATION

  公开号：EP0384392A1

  公开（公告）日：1990-08-29

  Aromatic halide is converted to aromatic nitrile, e.g., p-chlorobenzotrifluoride is converted to 4-(trifluoromethyl)benzonitrile, utilizing Ni(Pφ₃)₃ as a catalyst where said catalyst is formed starting with NiCl₂ or NiCl₂·6H₂O where formation of said catalyst starting with NiCl₂ or NiCl₂·6H₂O and conversion of halide to nitrile are carried out in a single reactor vessel. The method comprises the steps of (a) forming catalyst by steps comprising (i) forming essentially dry Ni(Pφ₃)Cl₂ in situ in said reactor vessel starting with NiCl₂ or NiCl₂·6H₂O, (ii) reacting said essentially dry Ni(Pφ₃)₂Cl₂ with Pφ₃ in the presence of a reducing metal in C₂-C₅ alcohol or aprotic polar reaction solvent in said reactor vessel to produce Ni(Pφ₃)₃ catalyst therein, and (b) adding said halide into said reactor vessel to form a complex in C₂-C₅ alcohol or aprotic polar reaction solvent from said halide and said catalyst and adding alkali metal cyanide to convert halogen to CN and thereby produce nitrile. When anhydrous NiCl₂ is a starting material, steps (a)(i) and (a)(ii) are preferably carried out as a single step where anhydrous NiCl₂ and at least three equivalents of Pφ₃ are added to C₂-C₅ alcohol or aprotic polar solvent followed by addition of reducing metal powder and reaction is carried out to convert NiCl₂ to Ni(Pφ₃)₃ with intermediate formation of Ni(Pφ₃)₂Cl₂. When NiCl₂·6H₂O is a starting material, essentially dry Ni(Pφ₃)₂Cl₂ is formed in step (a)(i) by forming an admixture thereof with azeotrope-forming liquid (e.g., anhydrous C₂-C₅ alcohol or aprotic polar solvent or toluene) and heating to distill off water and forming essentially dry NiCl₂ which is converted to essentially dry Ni(Pφ₃)₂Cl₂ or the NiCl₂·6H₂O is reacted with Pφ₃ to form wet Ni(Pφ₃)₂Cl₂ which is dried by forming an azeotropic mixture and distilling to remove water or by heating or the NiCl₂·6H₂O is made essentially dry by heating with or without Pφ₃ present in the absence of reaction solvent to flash off water and form essentially dry NiCl₂ which is reacted with Pφ₃. The preferred C₂-C₅ alcohol is t-butanol which minimizes formation of hydrodehalogenation side-product in step (b) compared to other alcohols. The preferred aprotic polar solvent is acetonitrile.

  芳香卤化物可以转化为芳香腈，例如，使用Ni(Pφ₃)₃作为催化剂，p-氯苯三氟甲烷可以转化为4-(三氟甲基)苯腈。所述催化剂由NiCl₂或NiCl₂·6H₂O开始形成，其中利用单个反应器容器进行所述催化剂的形成，开始于NiCl₂或NiCl₂·6H₂O，同时进行卤代物到腈的转化。该方法包括以下步骤：(a)通过以下步骤形成催化剂：(i)在反应器容器中开始形成基本干燥的Ni(Pφ₃)Cl₂，开始于NiCl₂或NiCl₂·6H₂O，(ii)在还原金属和C₂-C₅醇或无极性极性反应溶剂的存在下，在反应器容器中反应所述基本干燥的Ni(Pφ₃)₂Cl₂和Pφ₃，以在其中产生Ni(Pφ₃)₃催化剂，以及(b)将所述卤代物加入所述反应器容器中，以从所述卤代物和所述催化剂中形成C₂-C₅醇或无极性极性反应溶剂的复合物，并添加碱金属氰化物以将卤素转化为CN并因此产生腈。当无水NiCl₂为起始材料时，步骤(a)(i)和(a)(ii)最好作为单个步骤进行，其中将无水NiCl₂和至少三当量的Pφ₃加入C₂-C₅醇或无极性极性溶剂中，然后加入还原金属粉末并进行反应，以转化NiCl₂为Ni(Pφ₃)₃，中间形成Ni(Pφ₃)₂Cl₂。当NiCl₂·6H₂O为起始材料时，在步骤(a)(i)中通过将其与共沸液形成的液体（例如，无水C₂-C₅醇或无极性极性溶剂或甲苯）混合并加热以蒸馏水并形成基本干燥的NiCl₂，然后将其转化为基本干燥的Ni(Pφ₃)₂Cl₂，或者通过将NiCl₂·6H₂O与Pφ₃反应形成湿的Ni(Pφ₃)₂Cl₂，然后通过形成共沸混合物并蒸馏去除水或加热干燥来将其干燥，或者通过在无反应溶剂的情况下加热或不加Pφ₃的情况下加热，使NiCl₂·6H₂O基本干燥并闪蒸水，形成基本干燥的NiCl₂，然后与Pφ₃反应。首选的C₂-C₅醇是叔丁醇，与其他醇相比可以最小化步骤(b)中的脱卤反应副产物的形成。首选的无极性极性溶剂是乙腈。
• Process for producing bis( trifluoromethyl)benzaldehyde
  申请人：——

  公开号：US20020042541A1

  公开（公告）日：2002-04-11

  The invention relates to a process for producing a bis(trifluoromethyl)benzaldehyde represented by the general formula [1]. This process includes reacting a mono-substituted bis(trifluoromethyl)benzene, represented by the general formula [2], with carbon monoxide and hydrogen in the presence of a catalyst and a base, the catalyst including a palladium compound and a phosphine, 1 wherein X is a halogen atom selected from F, Cl, Br and I, a trifluoromethanesulfonate group, or a pentafluoroethanesulfonate group.

  本发明涉及一种生产由通式[1]表示的双(三氟甲基)苯甲醛的方法。该方法包括在催化剂和碱的存在下，将由通式[2]表示的单取代的双(三氟甲基)苯与一氧化碳和氢反应，所述催化剂包括钯化合物和膦化合物，其中X是从F、Cl、Br和I中选择的卤素原子、三氟甲烷磺酸基或五氟乙烷磺酸基。