4,5,6,7-tetrakis(methylthio)-1,3-benzodithiole-2-thione | 133148-79-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5,6,7-tetrakis(methylthio)-1,3-benzodithiole-2-thione
• 英文别名: 3,4,5,6-Tetrakis(methylthio)benzo-1,3-dithiol-thion；Tetrakis(methylthio)benzo-1,3-dithiol-2-thion；4,5,6,7-Tetrakis(methylsulfanyl)-1,3-benzodithiole-2-thione
• CAS: 133148-79-5
• 化学式: C₁₁H₁₂S₇
• 分子量: 368.678
• InChiKey: MWOOPKHEJKEKKR-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C(Solv: 1-butanol (71-36-3))
• 沸点：
  428.4±55.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  184
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrakis(methylthio)-1,3-benzodithiole-2-thione 在 亚磷酸三乙酯 作用下， 反应 2.0h， 以69%的产率得到per(methylthio)dibenzotetrathiafulvalene
  参考文献：
  名称：

  有机电子导体和前体-XII。新型二苯并四硫富瓦烯的合成

  摘要：

  合成了新的（有机硫基）取代的二苯并-1,3-四硫富瓦烯（DBTFF）。描述了的电荷转移配合物和的性质。

  DOI：

  10.1016/s0040-4039(00)79473-1
• 作为产物：
  描述：

  二硫化碳 、 hexasodium,benzene-1,2,3,4,5,6-hexathiolate 、 碘甲烷 以82%的产率得到4,5,6,7-tetrakis(methylthio)-1,3-benzodithiole-2-thione
  参考文献：
  名称：

  Organic Electronic Conductors and Precursors;¹Reaction of Hexasodium Benzene-hexathiolate and Benzenehexathiol with Carbon Disulfide

  摘要：

  六钠苯六硫醇（1）和苯六硫醇（7）与二硫化碳的反应被研究。根据反应条件和1或7与二硫化碳的摩尔比，可以得到1,3-苯并二硫杂环戊-2-硫酮（6）、2,6-二硫杂苯并[1,2-d:4,5-d']（5）、2,5-二硫杂苯并[1,2-d:3,4-d']双[1,3]二硫杂环戊（9）或2,5,8-三硫杂苯三[1,3]二硫杂环戊（2）。

  DOI：

  10.1055/s-1990-27120

文献信息

• Alkylthio-substituierte Bis(benzol-1,2-dithiolato)zinkate, Benzol-1,2-dithiole und -1,2-dithiolate - Edukte f�r Dibenzo[c,g](1,2,5,6)tetrathiocine und Benzo[c](1,2,3)-trithiole; Untersuchungen zu Benzodithieten und ortho-Dithiobenzochinonen
  作者：E. Fangh�nel、R. Herrmann、J. Bierwisch、H. Hartung、U. Baumeister、G. Maier、H. P. Reisenauer

  DOI：10.1002/prac.19943360512

  日期：——

  Using benzenehexathiolate 1 it is possible to synthesize alkylthio-substituted benzo-1,3-dithiole-2-thiones 2, or -ones 3 and benzo-di(1,3-dithiole-2-thiones) 4, or -ones 5, resp., which were cleaved under basic conditions. The generated benzene-1,2-dithiolates 7 were isolated as benzenedithiolato zincates 8, benzene-1,2-dithioles 11, and benzene-1-thiole-2-thiolates 10. Dibenzo[c,g](1,2,5,6)-tetrathiocins 9 were synthesized by oxidation of 7 or 8 in good yields. For the per(methylthio)-substituted tetrathiocin 9a the twist conformation was proved by x-ray structure analysis.The tetrathiocin 9a was probably formed via the orthodithiobenzoquinone 13a. Photolysis of 3a at room temperature in solution led to 9a and tetrakis(methylthio)benzo[c] (1,2,3)trithiole 12a as the main product, which was also formed by irradiation of 9a. The trithioles 12 were formed from 8 by reaction with sulfur dichloride. 12a was investigated by x-ray structure analysis. ortho-Dithiobenzoquinone 13c can be claimed as an intermediate upon irradiation of benzo-1,3-dithiol-2-one 3c in an argon matrix at 10 K. Depending on the wavelength the equilibrium lies either on the side of dithiobenzoquinone 13c or benzodithiete 14c. The same is true for system 15/16, which can be reached by flash vacuum pyrolysis of 3c.
• Fanghaenel, E.; Wegner, R.; Beye, N., Journal fur Praktische Chemie - Chemiker-Zeitung, 1995, vol. 337, # 4, p. 299 - 306
  作者：Fanghaenel, E.、Wegner, R.、Beye, N.、Peters, K.、Muellen, K.

  DOI：——

  日期：——
• RICHTER, A. M.;BEYE, N.;FANGHANEL, E., SYNTHESIS,(1990) N2, C. 1149-1151
  作者：RICHTER, A. M.、BEYE, N.、FANGHANEL, E.

  DOI：——

  日期：——
• Organic Electronic Conductors and Precursors;¹Reaction of Hexasodium Benzene-hexathiolate and Benzenehexathiol with Carbon Disulfide
  作者：A. M. Richter、N. Beye、E. Fanghänel

  DOI：10.1055/s-1990-27120

  日期：——

  The reaction of hexasodium benzenehexathiolate (1) and benzenehexathiol (7) with carbon disulfide is studied. Depending on the reaction conditions and the molar ratio of 1 or 7 to carbon disulfide the 1,3-benzodithiole-2-thiones 6, the 2,6-dithioxobenzo[1,2-d: 4,5-d′]- 5, the 2,5-dithioxobenzo[1,2-d: 3,4-d′]bis[1,3]dithiole 9 or the 2,5,8-trithioxobenzotris[1,3]dithiole (2) are obtained.

  六钠苯六硫醇（1）和苯六硫醇（7）与二硫化碳的反应被研究。根据反应条件和1或7与二硫化碳的摩尔比，可以得到1,3-苯并二硫杂环戊-2-硫酮（6）、2,6-二硫杂苯并[1,2-d:4,5-d']（5）、2,5-二硫杂苯并[1,2-d:3,4-d']双[1,3]二硫杂环戊（9）或2,5,8-三硫杂苯三[1,3]二硫杂环戊（2）。
• Organic electronic conductors and precursors - XII. Synthesis of novel dibenzotetrathiafulvalenes
  作者：Norbert Beye、Robby Wegner、Andreas M. Richter、Egon Fanghänel

  DOI：10.1016/s0040-4039(00)79473-1

  日期：1991.1

  New per(organylthio) substituted dibenzo-1,3-tetrathiafulvalenes (DBTFF) were synthesized. The properties of and of the charge-transfer complexes of are described.

  合成了新的（有机硫基）取代的二苯并-1,3-四硫富瓦烯（DBTFF）。描述了的电荷转移配合物和的性质。