2,3,7,8-四氯噻蒽 | 61656-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二硫类化合物
• 中文名称: 2,3,7,8-四氯噻蒽
• 英文名称: 2,3,7,8-tetrachlorothianthrene
• 英文别名: 2,3,7,8-tetrachlorothianthren
• CAS: 61656-02-8
• 化学式: C₁₂H₄Cl₄S₂
• 分子量: 354.108
• InChiKey: JCJOKFLPNGCLSA-UHFFFAOYSA-N

物化性质

• 沸点：
  468.5±45.0 °C(Predicted)
• 密度：
  1.663±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  18
• 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：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,7,8-四氯噻蒽 生成 1-chloro-thianthrene
  参考文献：
  名称：

  Process for manufacturing chlorothianthrenes

  摘要：

  在单氯甲苯中，硫菌素与过量氯在Lewis酸催化剂存在下反应，产生一种氯硫菌素混合物，其中主要成分是2,3,7,8-四氯硫菌素。从适当的溶剂，如四氢呋喃中重新结晶氯硫菌素混合物，可得到纯度大于90％的2,3,7,8-四氯硫菌素。

  公开号：

  US03989715A1
• 作为产物：
  描述：

  噻蒽 在 磺酰氯 作用下， 以 various solvent(s) 为溶剂， 反应 4.0h， 生成 2,3,7,8-四氯噻蒽
  参考文献：
  名称：

  Sulfur analogues of polychlorinated dibenzo-P-dioxins, dibenzofurans and diphenyl ethers as inducers of CYP1A1 in mouse hepatoma cell culture and structure-activity relationships

  摘要：

  AbstractThree sulfur containing compounds, 2,3,7,8 tetrachlorothianthrene (TCTA), 2,3,7,8 tetrachlorodibenzothiophene (TCDT), and 3,3,4,4 tetrachlorodiphenyl sulfide (TCDPS), were analyzed for their CYP1A1 inducing potencies – measured as aryl hydrocarbon hydroxylase (AHH) and 7 ethoxyresorufin O‐deethylase (EROD) activities – in mouse hepatoma cell culture Hepa 1 Marked differences in the induction potencies were observed among the three compounds studied and between 2,3,7,8 tetrachlorodibenzo p dioxin (TCDD) and its sulfur analogue The estimated EC50 values for TCDD, TCTA, and TCDT were about 8 pM, 700 pM, and 7 5 nM, respectively TCDPS did not elicit any AHH/EROD induction Comparative molecular field analysis (CoMFA) was not able to predict correctly the biological potency of TCTA and TCDT The most important reason for the poor performance of the model may be the positive point charge of sulfur in TCTA and TCDT

  DOI：

  10.1002/etc.5620130917

文献信息

• Verfahren zur Herstellung von 2-Chlor-4-nitro-alkylbenzol
  申请人：BAYER AG

  公开号：EP0399293A1

  公开（公告）日：1990-11-28

  Bei der Herstellung von 2-Chlor-4-nitro-alkylbenzol durch Umsetzung von 4-Nitro-alkylbenzol mit elementarem Chlor oder Chlor abgebenden Verbindungen in Gegenwart eines Friedel-Crafts-Katalysators in flüssiger Phase werden besonders hohe Selektivitäten bezüglich der aus­schließlich in 2-Position chlorierten Zielverbindungen erreicht, wenn als Co-Katalysator ein dibenzokonden­sierter Schwefelheterocyclus der Formel mit den in der Beschreibung angegebenen Bedeutungen für R¹ bis R⁸, X und n eingesetzt wird.

  在液相中，在弗里德尔-卡夫斯催化剂存在下，通过 4-硝基烷基苯与元素氯或供氯 化合物反应制备 2-氯-4-硝基烷基苯时，如果使用式如下的二苯并缩硫杂环作为助催 化剂，则对完全在 2 位氯化的目标化合物具有特别高的选择性 式中 R¹至 R⁸、X 和 n 的含义在描述中给出。
• The study on UV-degradation dynamics of 2,3,7,8-tetrachlorodibenza-p-dioxin and its analogues
  作者：Zhaohai Qin

  DOI：10.1016/0045-6535(96)00150-6

  日期：1996.7

  A study on UV-degradation dynamics of 2,3,7,8-tetrachlorodibenzo-p-dioxin (2,3,7,8-TCDD) and its analogues 2,3,7,8-tetrachlorophenoxthin (2,3,7,8-TCPT) and 2,3,7,8-tetrachlorothianthrene(2,3,7,8-TCTR) in solvents CHCl3 and CCl4 was completed. The results indicated that they were degradated by UV in different way in different solvent. The degradation of 2,3,7,8-TCDD and 2,3,7,8-TCPT are pseudo-first-order reactions in CHCl3, but complex reactions in CCl4; the degradation of 2,3,7,8-TCTR is a zero-order reaction in CHCl3, but a pseudo-first-order reaction in CCl4. All of the three compounds disappeared in CCl4 much faster than in CHCl3 under 254 nm UV-irradiation. Copyright (C) 1996 Elsevier Science Ltd
• Sulfuryl chloride in the synthesis of derivatives of dibenzothiophene, phenoxathiin, and thianthrene
  作者：E. D. Savin、V. I. Nedel'kin、D. V. Zverev

  DOI：10.1007/bf02253114

  日期：1997.3
• Elimination kinetics and toxicity of 2,3,7,8-tetrachlorothiantheren, a thio analogue of 2,3,7,8-TCDD
  作者：R. Weber、H. Hagenmaier、D. Schrenk

  DOI：10.1016/s0045-6535(97)10227-2

  日期：1998.5

  In comparison to the polychlorinated dibenzo-p-dioxins (PCDD) informations on their thio analogues the polychlorinated thianthrens (PCTA) are very limited. In this study we investigated the kinetics and toxicity of 2,3,7,8-tetrachlorothianthren (TCTA), the analogue of the most toxic PCDD congener 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). It was found that TCTA is rapidly eliminated in mouse liver homogenate fortified with an NADPH-regenerating system suggesting rapid metabolic degradation by liver monooxygenases. Furthermore, TCTA. was rapidly eliminated from mouse liver and whole body. In accordance with this rapid elimination, a weekly dosage of 1 mg TCTA per kg body weight (i.p.) over six weeks did not result in weight loss or other signs of overt toxicity in male mice. In rat hepatocytes in primary culture, TCTA was active as inducer of dioxin receptor-regulated cytochrome P4501A1 activity measured as 7-ethoxyresorufin O-deethylase (EROD). The relative inducing potency was about 0.0001 in comparison to TCDD. In spite of this molecular effects, the rapid elimination both in vitro and in vivo argues against a consideration of a TCDD equivalency factor for TCTA. (C) 1998 Elsevier Science Ltd All rights reserved.
• Kopponen Paeivi, Sinkkonen Seija, Poso Antti, Gynther Jukka, Kaerenlampi +, Environ. Toxicol. and Chem., 13 (1994) N 9, S 1543-1548
  作者：Kopponen Paeivi, Sinkkonen Seija, Poso Antti, Gynther Jukka, Kaerenlampi +

  DOI：——

  日期：——