6-Chloro-1,2,3-benzodithiazol-1-ium chloride | 35576-53-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 6-Chloro-1,2,3-benzodithiazol-1-ium chloride
• 英文别名: 6-chloro-benzo-1,2,3-dithiazolium chloride；6-chloro-1,2,3-benzodithiazolium chloride；6-chloro-benzo[1,2,3]dithiazolylium; chloride；6-chloro-benzo[1,2,3]dithiazolium; chloride；6-Chlor-benzo[1,2,3]dithiazolylium; Chlorid；6-Chlor-benzo[1,2,3]dithiazolium; Chlorid；6-Chloro-1,2,3-benzodithiazol-1-ium;chloride
• CAS: 35576-53-5；3292-56-6
• 化学式: C₆H₃ClNS₂*Cl
• 分子量: 224.135
• InChiKey: FLLNQVZOFGKYEW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chloro-1,2,3-benzodithiazol-1-ium chloride 在 sodium acetate 、 N,N-二甲基苯胺 作用下， 反应 1.5h， 生成 6-氯-2-苯基-1,3-苯并噻唑
  参考文献：
  名称：

  A New Synthesis of 2-Arylbenzothiazoles from 1,2,3-Benzodithiazole-2-Oxides

  摘要：

  The reaction of 6-substituted-1,2,3-benzodithiazole-2-oxides (3a-3d) with aromatic aldehydes, carboxylic acids, and their chlorides in the presence of an organic base provides a new method for the synthesis of 6-substituted-2-arylbenzothiazoles (4a-4d) without involving the preparation of intermediate 2-aminobenzenethiols.

  DOI：

  10.1080/00397919308009777
• 作为产物：
  描述：

  4-氯苯胺盐酸盐 在 二氯化二硫 、 溶剂黄146 作用下， 生成 6-Chloro-1,2,3-benzodithiazol-1-ium chloride
  参考文献：
  名称：

  Bessubetz; Ignatjuk-Maisstrenko, Zhurnal Prikladnoi Khimii, 1939, vol. 12, p. 1138

  摘要：

  DOI：

文献信息

• Reaction of Herz salts with malononitrile: a general route to (6H-1,2,3-benzodithiazol-6-ylidene)malononitriles
  作者：Panayiotis A. Koutentis、Charles W. Rees

  DOI：10.1039/b110024f

  日期：2002.1.23

  6-Chloro-1,2,3-benzodithiazolium chlorides 1 (Herz salts) react with malononitrile to afford the highly coloured ylidenes 2 in low to moderate yields. The reaction is general but complex and in the case of the 6-chloro-4-methoxy-1,2,3-benzodithiazolium chloride 1e the by-products 6-chloro-4-methoxy-1,3-benzothiazole-2-carbonitrile 3, 6-chloro-4-methoxy-2,3-dihydro-1,3-benzothiazole-2,2-dicarbonitrile 4, and 4-methoxy-6-thiocyanato-1,3-benzothiazole-2-carbonitrile 5 were also isolated.

  6-氯-1,2,3-苯并二噻唑氯化物1（赫兹盐）与丙二腈反应，以低至中等产率得到高度着色的亚甲基化合物2。该反应具有普遍性，但复杂性较高。在6-氯-4-甲氧基-1,2,3-苯并二噻唑氯化物1e的情况下，还分离出了副产物6-氯-4-甲氧基-1,3-苯并噻唑-2-氰化物3、6-氯-4-甲氧基-2,3-二氢-1,3-苯并噻唑-2,2-二氰化物4和4-甲氧基-6-硫氰酸基-1,3-苯并噻唑-2-氰化物5。
• Pharmaceutical composition and method for treating cardiovascular
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05116851A1

  公开（公告）日：1992-05-26

  A novel pharmaceutical composition and method is disclosed for the treatment of cardiovascular diseases, e.g. myocardial ischemia and/or arrhythmia. The method and composition include an effective amount of a compound of the formula ##STR1## wherein X, Y, R, R.sub.1, A, A', m, n, p, p' and B are as defined herein.

  本发明揭示了一种用于治疗心血管疾病，例如心肌缺血和/或心律失常的新型药物组合物和方法。该方法和组合物包括式中化合物的有效量##STR1##其中X、Y、R、R.sub.1、A、A'、m、n、p、p'和B如本文所定义。
• A straightforward synthesis of 2-aminobenzothiazoles from Herz compounds
  作者：Ana G. Neo、Rosa M. Carrillo、Carlos F. Marcos

  DOI：10.1039/c1ob05398a

  日期：——

  2-Aminobenzothiazoles are readily synthesised from anilines, sulfur monochloride and isocyanides. The key step consists of an iodine-catalysed insertion of isocyanides into the S–S bond of hydrolysed Herz salts, with concomitant extrusion of sulfur monoxide.

  2-氨基苯并噻唑很容易从苯胺合成， 一氯化硫和异氰化物。关键步骤包括将碘催化的异氰酸酯插入水解的Herz盐的S–S键中，并同时挤出一氧化硫。
• The action of sulphur monochloride on aromatic primary amines: the Herz reaction
  作者：P. Hope、L. A. Wiles

  DOI：10.1039/j39670001642

  日期：——

  chlorides are obtained by the action of sulphur monochloride on a primary aromatic amine, its salts, or N-acyl derivatives. Four reactions are involved, (i) the formation of the heterocyclic ring, (ii) the chlorination of the aromatic ring, (iii) replacement of electron-attracting groups in the ortho- and para-positions by chlorine, and (iv) the oxidation of the sulphur atom in position 2. A likely

  通过一氯化硫对伯芳族胺，其盐或N-酰基衍生物的作用获得1,3,2-苄硫唑硫鎓氯化物。涉及四个反应，（i）杂环的形成，（ii）芳环的氯化，（iii）用氯取代邻位和对位的吸引电子的基团，和（iv） 2位硫原子的氧化。考虑了可能的反应顺序，并提供了支持每个阶段的实验证据。
• A novel sulfur–nitrogen π-heterocyclic radical anion, (6H-1,2,3-benzodithiazol-6-ylidene)malononitrilidyl, and its homo- and heterospin salts
  作者：Alexander Yu. Makarov、Elena A. Chulanova、Nikolay A. Semenov、Nikolay A. Pushkarevsky、Anton V. Lonchakov、Artem S. Bogomyakov、Irina G. Irtegova、Nadezhda V. Vasilieva、Enno Lork、Nina P. Gritsan、Sergey N. Konchenko、Victor I. Ovcharenko、Andrey V. Zibarev

  DOI：10.1016/j.poly.2014.01.027

  日期：2014.4

  (6H-1,2,3-Benzodithiazol-6-ylidene)malononitrile (4) was electrochemically and chemically reduced with tetrakis(dimethylamino)ethylene (TDAE) and CrTo1(2) into the title radical anion (5). The electrochemically generated 5 and its salts [TDAE](2+)[5](2) (7) and [CrTol(2)]* [5] (8) were characterized by solution EPR in combination with UV-Vis spectroscopy. Salts 7 and 8 were isolated and characterized by elemental analysis and solid-state EPR, and 8 by magnetic measurements in the temperature range 2-300 K. The value of the effective magnetic moment of the salt 8 at 300 K, mu eff = 1.64 (mu B), indicates n-dimerization of 5 in the solid state. For the molar magnetic susceptibility x of 8, the temperature dependences of xT and 1/ x in the range 2-300 K can be approximated by the Curie-Weiss law with the Curie-Weiss constant C and temperature 1', equal to 0.33 0.01 cm3 K mo1-1 and -1.0 0.1 K, respectively. In the mean-field approximation, the effective value of the exchange interaction of [CrTol(2)]C with its neighboring cations can be estimated as 41= -1.4 cm-1. All the experimental results were supported by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.

  (6H-1,2,3-苯并二噻唑-6-基亚基)丙二腈(4)用电化学和化学还原方法,使用四(二甲基氨基)乙烯(TDAE)和CrTol2(2),得到了标题的自由基阴离子(5)。电化学产生的5及其盐[TDAE](2+)[5](2)(7)和[CrTol(2)]*[5](8)通过结合溶液EPR和UV-Vis光谱进行了表征。盐7和8已被分离并通过元素分析和固体EPR表征,其中8还通过在2-300 K温度范围内的磁测量进行了表征。盐8在300 K时的有效磁矩值,mueff=1.64(mB),表明5在固态中形成n聚体。对于8的摩尔磁感_x,在2-300 K范围内,xT和1/x的温度依赖性可近似地表示为居里-魏斯定律,其居里-魏斯常数C和温度发出,分别为0.33±0.01 cm3 K mol-1和-1.0±0.1 K。在平均场近似下,可以估计[CrTol(2)]C与其邻近阳离子之间的交换相互作用的有效值为41= -1.4 cm-1。所有实验结果均通过DFT计算得到了支持。(C)2014 Elsevier Ltd.保留所有权利。