6-choro-2,3-dimethylbenzothiazolium iodide | 2896-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-choro-2,3-dimethylbenzothiazolium iodide
• 英文别名: 2,3-dimethyl-5-chlorobenzothiazolium iodide；5-chloro-2,3-dimethyl-benzothiazolium; iodide；5-Chlor-2,3-dimethyl-benzothiazolium; Jodid；5-Chloro-2,3-dimethyl-1,3-benzothiazol-3-ium iodide；5-chloro-2,3-dimethyl-1,3-benzothiazol-3-ium;iodide
• CAS: 2896-42-6
• 化学式: C₉H₉ClNS*I
• 分子量: 325.601
• InChiKey: WBFLKOCWIMYELE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-choro-2,3-dimethylbenzothiazolium iodide 、 2-[4-(N-acetyl-anilino)-buta-1,3-dienyl]-3-methyl-benzooxazolium; iodide 在 三乙胺 作用下， 以 乙醇 、 甲醇 为溶剂， 反应 1.0h， 以67%的产率得到5-chloro-3-methyl-2-(5-(3-methylbenzoxazol-2(3H)-ylidene)penta-1,3-dien-1-yl)benzothiazol-3-ium chloride
  参考文献：
  名称：

  Third-order nonlinear optical properties of unsymmetric pentamethine cyanine dyes possessing benzoxazolyl and benzothiazolyl groups

  摘要：

  A series of unsymmetric pentamethine cyanine dyes featuring benzoxazolyl and benzothiazolyl groups were synthesized, the structures were characterized by H-1 NMR, UV-vis absorption spectroscopy and mass spectrometry. The dyes with different anions such as chloride, tetraphenylborate and tetra(4-fluorophenyl)borate were also obtained and their solubility can be changed by the choice of the anion part. The third-order nonlinear optical properties were measured by the Z-scan technique with a pico-second laser beam at 532 nm in DMF solution. The third-order nonlinear optical susceptibilities chi((3)) and the second-order hyperpolarizabilities gamma' were obtained. The results reveal that these dyes exhibit strong reverse saturable absorption and nonlinear refraction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.07.007
• 作为产物：
  描述：

  5-氯-2-甲基苯并噻唑 、 碘甲烷 以Ca.67 %的产率得到6-choro-2,3-dimethylbenzothiazolium iodide
  参考文献：
  名称：

  [EN] CYANINE DYE AND PREPARATION METHOD THEREFOR AND USE THEREOF, SAMPLE ANALYSIS METHOD, AND ANALYZER
  [FR] COLORANT CYANINE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION, PROCÉDÉ D'ANALYSE D'ÉCHANTILLON ET ANALYSEUR
  [ZH] 花菁染料、其制备方法、用途、样本分析方法及分析仪

  摘要：

  涉及荧光染料，特别涉及花菁染料、其制备方法及其用途。具体地，提供了具有如通式I所示结构的化合物或其水合物、溶剂化物、立体异构体、互变异构体或晶型，其中，R1、R2、R3如说明书所定义。提供的花菁染料具有稳定性好、生物穿透力好等优点。

  公开号：

  WO2024017247A1

文献信息

• 一种一甲川菁染料的合成方法
  申请人：付义乐

  公开号：CN105885466A

  公开（公告）日：2016-08-24

  本发明涉及一种一甲川菁染料的合成方法，其包括以下步骤：(1)将N-甲基喹啉-2-硫酮、对甲苯磺酸甲酯、含有活性甲基的杂环季铵盐以及无水乙醇加入圆底烧瓶中，滴入三乙胺，回流；(2)将上述步骤(1)回流后的溶液经减压蒸出部分溶剂，冷却，待有固体析出，再进行抽滤，干燥，重结晶，以最终得到一甲川菁染料成品。本发明操作简单，合成产率高、步骤少且时间短，能有效避免中间产物的纯化处理，合成效率高，合成成本较低。
• The Synthesis and Spectral Properties of Some New Monomethine Cyanine Dyes for Live Cell Imaging
  作者：Y. L. Fu、S. Y. Dong、Y. Z. Zhou、G. Zhang、Q. C. Yang、X. Zhai、L. Y. Wang

  DOI：10.1002/bkcs.10110

  日期：2015.2

  Four monomethine cyanine dyes were synthesized and their structures were confirmed by ¹H NMR, IR, UV–Vis, and HRMS. Their spectral properties were studied. It could be found that the λ_max of the dyes was shorter in the protonic solvents compared with that in the non‐protonic solvents. Moreover, the λ_max shows a hypsochromic shift with the increasing polarity of the solvents. The interactions of four dyes with DNA were also studied. The results showed that the fluorescence intensities of the dyes 3a and 3b took place a qualitative change in the presence of DNA compared with the free dyes. The dyes used as cellular imaging agents were researched. The results indicated that the dye 3b could penetrate the live cell membrane.

  合成了四种一甲基氰基染料，并通过 1H NMR、IR、UV-Vis 和 HRMS 确认了它们的结构。研究了它们的光谱特性。研究发现，与在非质子溶剂中相比，染料在质子溶剂中的λmax 更短。此外，随着溶剂极性的增加，λmax 出现了低色移。还研究了四种染料与 DNA 的相互作用。结果表明，与游离染料相比，染料 3a 和 3b 在 DNA 存在时的荧光强度发生了质的变化。研究了用作细胞成像剂的染料。结果表明，染料 3b 可以穿透活细胞膜。
• Efficient One-Pot Three-Component Synthesis of Monomethine Cyanine Dyes with Quinoline Nucleus and Their Spectral Properties
  作者：Y.L. Fu、B.R. Zhang、S. Wang、X.X. Gao、L.Y. Wang

  DOI：10.5012/bkcs.2013.34.2.489

  日期：2013.2.20

  An improved method for the preparation of monomethine cyanine dyes with quinoline nucleus by one-pot three-component using 1-methyl-2-quinolinethione, quaternized 2- or 4-methylheterocyclic compounds and methyl p-toluenesulfonate as starting materials was described. Compared with the traditional methods, the new synthetic method reduced the reaction steps, shortened the reaction time, avoided the separation

  介绍了以1-甲基-2-喹啉硫酮、季铵化2-或4-甲基杂环化合物和对甲苯磺酸甲酯为起始原料的一锅三组分制备具有喹啉核的单甲炔花青染料的改进方法。与传统方法相比，新的合成方法减少了反应步骤，缩短了反应时间，避免了中间体的分离纯化，降低了成本。染料在478.0-563.0 nm范围内吸收，摩尔消光系数为1.3 × 10 4 -9 .4 × 10 4 L mol ×1 cm ×1 。它们在不同溶剂中的荧光最大值和斯托克斯位移分别在 525.2-594.4 nm 和 16.2-80.6 nm 范围内。从染料在不同溶剂中的光谱性质来看，
• Koenig, Chemische Berichte, 1928, vol. 61, p. 2070
  作者：Koenig

  DOI：——

  日期：——
• Metzger,J. et al., Bulletin de la Societe Chimique de France, 1964, p. 2888 - 2897
  作者：Metzger,J. et al.

  DOI：——

  日期：——