chloro-5 dihydroxy-2,4' biphenyle | 106539-32-6

• 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: chloro-5 dihydroxy-2,4' biphenyle
• 英文别名: 2,4'-Dihydroxy-5-chlorobiphenyl；5-chloro-2,4'-dihydroxybiphenyl；5-chloro-2,4'dihydroxybiphenyl；5-chlorobiphenyl-2,4'-diol；5-Chlor-2,4'-dihydroxy-biphenyl；4-chloro-2-(4-hydroxyphenyl)phenol
• CAS: 106539-32-6
• 化学式: C₁₂H₉ClO₂
• 分子量: 220.655
• InChiKey: OPAHIYVGXFZZJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2907299090

反应信息

• 作为产物：
  描述：

  对氯苯酚 以 水 为溶剂， 反应 30.0h， 生成 chloro-5 dihydroxy-2,4' biphenyle
  参考文献：
  名称：

  光解后含一氯酚的冰的毒性增加：环境后果

  摘要：

  用细菌发光试验（费氏弧菌）和二恶英样效应的体外生物标志物测定（诱导H4IIE-luc 细胞中的 AhR 依赖性荧光素酶）并与水相中相同光反应产物的毒性作用进行比较。耦合冰样品中形成的光产物（来自 2-CP 光解的 3'-氯联苯-2,4'-二醇和 3-氯联苯-2,2'-二醇和来自 4-CP 光解的 5-氯联苯-2,4'-二醇) 被发现对 V.fisheri 的毒性高于亲本 CP，并引起显着的类二恶英效应（有效浓度 EC50 约为 3 x 10(-5) mol L(-1) 对应于已知较弱的 AhR 配体，例如非平面多氯联苯或多环芳烃）。为了完成图片，合成了由 4-CP (5-chlorobiphenyl-2,4'-diol) 形成的光产物，并用纯化化合物进行了详细的毒性评估，证实了用辐照样品获得的结果。我们的研究结果支持最近提出的模型，根据该模型，太阳辐射可以触发极地冰或对流层冰云颗粒中新型有

  DOI：

  10.1021/es035076k

文献信息

• Aryl Cations from Aromatic Halides. Photogeneration and Reactivity of 4-Hydroxy(methoxy)phenyl Cation
  作者：Stefano Protti、Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1021/jo049770+

  日期：2004.5.1

  cyclohexane and a heterolytic path in alcohols. Heterolysis of 1 and 2 in methanol and 2,2,2-trifluoroethanol offers a convenient access to triplet 4-hydroxy- and 4-methoxyphenyl cations. These add to π nucleophiles, viz., 2,3-dimethyl-2-butene, cyclohexene, and benzene, giving the arylated products in medium to good yields. Wagner−Meerwein hydride and alkyl migration are evidence for the cationic mechanism

  已在多种溶剂中检查了4-氯苯酚（1）和4-氯苯甲醚（2）的光化学，发现其主要通过环己烷中的均相路径和醇中的杂合路径导致还原性脱卤化反应。1和2的杂解甲醇和2,2,2-三氟乙醇中的二甲基甲酰胺提供了便捷的途径获得三重态4-羟基和4-甲氧基苯基阳离子 这些添加到π亲核试剂中，即2，3-二甲基-2-丁烯，环己烯和苯，以中等至良好的收率得到芳基化产物。Wagner-Meerwein氢化物和烷基迁移是烯烃加成的阳离子机理的证据。在非质子极性溶剂（如MeCN和乙酸乙酯）中，也可以合理地通过激基复合物并在一定程度上与捕集阱的亲核性成正比（2,3-二甲基-2-丁烯>环己烯≫），在一定程度上获得了芳构化（无重排）苯）。
• Electron-Transfer Oxidation of Chlorophenols by Uranyl Ion Excited State in Aqueous Solution. Steady-State and Nanosecond Flash Photolysis Studies
  作者：Mohamed Sarakha、Michèle Bolte、Hugh D. Burrows

  DOI：10.1021/jp993676t

  日期：2000.4.1

  The oxidation of chlorophenols by photoexcited uranyl ion was studied in aqueous solution at concentrations where the ground-state interactions were negligible. Nanosecond flash photolysis showed that a clean electron-transfer process from the chlorophenols to the excited uranyl ion is involved. This is suggested to lead to the formation of a U(V)/chlorophenoxyl radical pair complex. The efficiency

  在水溶液中研究了光激发铀酰离子对氯酚的氧化作用，其基态相互作用可忽略不计。纳秒闪光光解表明，涉及从氯酚到激发的铀酰离子的干净电子转移过程。这被认为导致形成 U(V)/氯苯氧基自由基对复合物。这种电荷转移过程的效率对于三种氯酚来说是统一的。然而，低产物产率表明，在没有氧气的情况下，在自由基对内以及从分离的铀 (V) 到苯氧基自由基的反电子转移似乎是主要的反应途径。在氧气存在下，氯苯酚消失和光产物形成的量子产率增加。
• Poly(aryl ether)polymer containing compositions
  申请人：AMOCO CORPORATION

  公开号：EP0090404A1

  公开（公告）日：1983-10-05

  Described herein are molding compositions comprising a blend of a poly(arylether) polymer, a styrene and/or acrylic copolymers and a compatibilizing amount of a polyhydroxyether.

  本文描述的模塑组合物包含聚芳基醚聚合物、苯乙烯和/或丙烯酸共聚物以及相容量的聚羟基醚的混合物。
• Formation and Reactivity of 4-Oxocyclohexa-2,5-dienylidene in the Photolysis of 4-Chlorophenol in Aqueous Solution at Ambient Temperature
  作者：Gottfried Grabner、Claire Richard、Gottfried Koehler

  DOI：10.1021/ja00104a029

  日期：1994.12

  Nanosecond laser flash photolysis of an aqueous solution of 4-chlorophenol (lambda(exc) = 266 nm) produces, at pulse end, a transient with absorption maxima at 384, 370, and ca. 250 nm; upon addition of an H-donor such as 2-propanol, this spectrum is converted into that of the phenoxyl radical (lambda(max) = 400 and 385 nm), and in presence of O-2, it is converted into a transient with a broad absorption band peaking at 460 nm. This reaction behavior can be understood by assuming formation of the carbene, 4-oxocyclohexa-2,5-dienylidene, by elimination of HCl from excited 4-chlorophenol; the pulse end transient spectrum is assigned to this species, while the 460 nm band is assigned to benzoquinone O-oxide formed by addition of O-2 to the carbene. Both phenoxyl radical and benzoquinone O-oxide are produced upon photolysis of 4-chlorophenol in neat alkanols as well. On the other hand, photolysis in n-hexane yields the triplet-triplet absorption, which is absent in polar solvents, and no indication of carbene formation. It can be concluded that the primary step of 4-chlorophenol photolysis in aqueous or alcoholic solution is heterolytic C-Cl bond scission; a quantum yield of 0.75 is determined for it in neutral or acid aqueous medium upon excitation at 266 nm. Photolysis of chlorophenolate produces the same transients, but with a markedly lower yield, and, in addition, e(aq)(-) and 4-chlorophenoxyl radicals. The proposed reaction mechanism provides a straightforward explanation of the results of photoproduct analysis, published by previous authors as well as contributed in the present work. In particular, formation of p-benzoquinone in the presence of O-2 can be accounted for by intermediate formation of benzoquinone O-oxide. Production of 4-oxocyclohexa-2,5-dienylidene with high yield allows, for the first time, extensive investigation of the kinetics and mechanism of the reactions of a carbene in an aqueous environment. In the present work, we have studied (a) the addition reaction with O-2 on the one hand and with halides on the other; (b) H abstraction reactions with alkanols; (c) reaction with 4-chlorophenol itself; and (d) reaction with H2O. The rate constants for reaction with O-2 (3.5 x 10(9) M(-1) s(-1)) and with I- (4.6 x 10(9) M(-1) s(-1)) are close to the diffusion-controlled limit, whereas reactions with Br- (6.8 x 10(7) M(-1) s(-1)) and Cl- (<3 x 10(5) M(-1) s(-1)) are slower. Rate constants for reaction with alkanols follow the pattern known for their reactions with radicals, with values ranging from 5 x 10(5) M(-1) s(-1) for tert-butyl alcohol to 1.9 x 10(7) M(-1) s(-1) for 2-butanol. All these observations are consistent with the triplet character of the carbene. A rate constant of 1.5 x 10(3) M(-1) s(-1) has been determined for reaction with H2O. This reaction is not accompanied by formation of OH radicals; it is concluded that it proceeds by insertion into the O-H bond rather than by O-H cleavage. The exceptional stability of the carbene in aqueous solution is thus mainly attributed to the high barrier for O-H rupture in the water molecule. Additionally, a specific carbene-H2O interaction is revealed by semiempirical calculations, which could contribute to energetic and orientational hindrance of the reaction. Further theoretical results support the interpretation of both spectroscopic and kinetic properties of the carbene.
• Boule, P.; Guyon, Cl.; Tissot, Annie, Journal de Chimie Physique et de Physico-Chimie Biologique, 1985, vol. 82, # 5, p. 513 - 516
  作者：Boule, P.、Guyon, Cl.、Tissot, Annie、Lemaire, J.

  DOI：——

  日期：——