2,3,8-trichlorodibenzothiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,3,8-trichlorodibenzothiophene
• 英文别名: 2,3,8-Trichloro-dibenzothiophene
• 化学式: C₁₂H₅Cl₃S
• 分子量: 287.597
• InChiKey: VCYNUWVCAJCEOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4,5-三氯苯胺 在 sodium nitrite 作用下， 以 sodium hydroxide 、 环己烷 、 硫酸 为溶剂， 反应 10.0h， 生成 2,3,8-trichlorodibenzothiophene
  参考文献：
  名称：

  Synthesis of Cl2- to Cl4-diphenylsulfides and Cl1- to Cl3-dibenzothiophenes

  摘要：

  The synthesis of eleven environmentally relevant mono-, di- and trichlorodibenzothiophenes (2) by photochemical ring-closure of polychlorodiphenylsulfides (1) is described. Ail monochlorodibenzothiophenes were additionally synthesized starting with a chlorothiophenol in a three-step reaction adapted from the synthesis of methyldibenzothiophenes. (C) 1999 Elsevier Science Ltd All rights reserved.

  DOI：

  10.1016/s0045-6535(98)00582-7

文献信息

• Palladium(<scp>ii</scp>)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
  作者：Mamoru Tobisu、Yoshihiro Masuya、Katsuaki Baba、Naoto Chatani

  DOI：10.1039/c5sc04890g

  日期：——

  A new process has been developed for the palladium(II)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of C–H and C–S bonds. In contrast to the existing methods for the synthesis of this scaffold by C–H functionalization, this new catalytic C–H/C–S coupling method does not require the presence of an external stoichiometric oxidant or reactive functionalities such as C–X or S–H

  开发了一种通过C-H 和 C-S 键裂解钯 ( II ) 催化合成二苯并噻吩衍生物的新工艺。与现有的通过 C-H 官能化合成该支架的方法相比，这种新的催化 C-H/C-S 偶联方法不需要存在外部化学计量氧化剂或反应性官能团，例如 C-X 或 S -H，允许其应用于复杂的 π 系统的合成。值得注意的是，该反应的产物形成步骤在于氧化加成步骤而不是还原消除步骤，使得该反应在机理上不常见。
• Identification and level estimation of chlorinated neutral aromatic sulfur compounds and their alkylated derivatives in pulp mill effluents and sediments
  作者：Seija Sinkkonen、Erkki Kolehmainen、Jaakkko Paasivirta、Jaana Koistinen、Mirja Lahtipera、Reino Lammi

  DOI：10.1016/0045-6535(94)90175-9

  日期：1994.6

  Seven effluent samples from a modern pulp mill, in which chlorine and chlorine dioxide bleaching is used, and five sediment samples from the recipient watercourse were investigated for polychlorinated dibenzothiophenes (PCDBTs), polychlorinated thianthrenes (PCTAs), polychlorinated diphenylsulfides (PCDPSs) and for alkylated derivatives of these. Mainly di-, tri-, tetra- and pentachlorinated congeners were studied. Particles and filtrates from the effluents were analyzed separately. The concentration levels of the nonalkylated compounds were found to be higher in the filtrates than in the particles. Trichlorinated dibenzothiophenes and thianthrenes were found as the major congeners. Pentachlorinated derivatives were not found. Alkylated di- and trichlorodibenzothiophenes were detected in some samples, while alkylated chlorinated thianthrenes and diphenylsulfides were nondetectable. The estimated concentration levels of the compounds detected were in the range of 40-2700 pg/L in the pulp mill effluents and in the range of 2-40 pg/g dry weight in the sediments. Mixtures of methylated di- and trichlorodibenzothiophenes used as references in analyses were prepared from methylchlorobiphenyls. Some new pure model compounds were obtained by HPLC fractionation of the chlorination mixture of dibenzothiophene. Structures of these were determined by H-1 NMR.