3,5-dinitro-1-phenylsulfonylbenzene | 214601-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dinitro-1-phenylsulfonylbenzene
• 英文别名: 3,5-dinitrodiphenyl sulfone；1-(benzenesulfonyl)-3,5-dinitrobenzene
• CAS: 214601-69-1
• 化学式: C₁₂H₈N₂O₆S
• 分子量: 308.271
• InChiKey: NJTCJHJEQZEKTI-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  504.4±40.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-dinitro-1-phenylsulfonylbenzene 在 三氯化铁 、 potassium carbonate 、 甲烷 、 肼 作用下， 以 N-甲基吡咯烷酮 、 甲醇 为溶剂， 反应 15.0h， 生成 3-phenoxy-5-phenylsulfonylaniline
  参考文献：
  名称：

  芳基3,5-二硝基苯基砜和亚砜的合成。3,5-二硝基二苯砜在与O-和S-亲核试剂反应中的转化

  摘要：

  1-Arylthio-3,5-dinitrobenzenes are selectively oxidized to the corresponding sulfones and sulfoxides by the action of hydrogen peroxide. Reactions of 3,5-dinitrodiphenyl sulfone with O- and S-centered nucleophiles (RXH, X = O, S) in dipolar aprotic solvents in the presence of K2CO3 result in replacement of the nitro group by the RX fragment; the reaction with methanol occurs in aqueous medium in the presence of NaHCO3. Substitution of the nitro group in 3,5-dinitrodiphenyl sulfone by phenylthio group, followed by oxidation of the sulfur atom to SO, and further replacement of the remaining nitro group yields 1,3,5-tris-(phenylsulfonyl)benzene. The phenylsulfonyl group in the latter is replaced by phenylthio group by reaction with PhSH in the presence of K2CO3. Mononitrosulfones obtained by nucleophilic substitution in the title compound can be reduced to the corresponding anilines.

  DOI：

  10.1023/a:1022563529344
• 作为产物：
  描述：

  3,5-dinitro-1-phenylthiobenzene 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以93%的产率得到3,5-dinitro-1-phenylsulfonylbenzene
  参考文献：
  名称：

  芳基3,5-二硝基苯基砜和亚砜的合成。3,5-二硝基二苯砜在与O-和S-亲核试剂反应中的转化

  摘要：

  1-Arylthio-3,5-dinitrobenzenes are selectively oxidized to the corresponding sulfones and sulfoxides by the action of hydrogen peroxide. Reactions of 3,5-dinitrodiphenyl sulfone with O- and S-centered nucleophiles (RXH, X = O, S) in dipolar aprotic solvents in the presence of K2CO3 result in replacement of the nitro group by the RX fragment; the reaction with methanol occurs in aqueous medium in the presence of NaHCO3. Substitution of the nitro group in 3,5-dinitrodiphenyl sulfone by phenylthio group, followed by oxidation of the sulfur atom to SO, and further replacement of the remaining nitro group yields 1,3,5-tris-(phenylsulfonyl)benzene. The phenylsulfonyl group in the latter is replaced by phenylthio group by reaction with PhSH in the presence of K2CO3. Mononitrosulfones obtained by nucleophilic substitution in the title compound can be reduced to the corresponding anilines.

  DOI：

  10.1023/a:1022563529344

文献信息

• Replacement of one nitro group in 1,3,5-trinitrobenzene and its analogs under the action of secondary aliphatic amines
  作者：M. A. Korolev、M. D. Dutov、S. A. Shevelev

  DOI：10.1007/bf02494836

  日期：1999.9
• Reaction of polyfluorinated alcohols with 1,3,5-trinitrobenzene and its analogs
  作者：S. A. Shevelev、M. D. Dutov、M. A. Korolev、O. Yu. Sapozhnikov、A. L. Rusanov

  DOI：10.1007/bf02495630

  日期：1998.8
• New procedure for nucleophilic sulfonation of aromatic nitro compounds: Destructive oxidation of S-arylthioglycolic acids esters
  作者：M. D. Dutov、O. V. Serushkina、S. A. Shevelev

  DOI：10.1134/s1070428007080131

  日期：2007.8

  A new reaction was discovered: oxidative destruction of sulfides of ArSCH(2)CO(2)Me type to sulfonic acids ArSO(3)H effected by 70% HNO(3). This reaction was used to introduce an SO(3)H group instead of aromatic nitro group activated only by meta-substituents: At treating with HSCH(2)CO(2)Me + K(2)CO(3) the NO(2) group was substituted to form ArSCH(2)CO(2)Me with subsequent transformation into ArSO(3)H. p-Fluoronitrobenzene behaved similarly (with replacement of the fluorine).
• Interaction of Hexamethylphosphoric Triamide with m-dinitrobenzenes
  作者：Mikhail D. Dutov、Olga V. Serushkina

  DOI：10.1016/j.mencom.2013.05.019

  日期：2013.5

  Heating of 1-X-3,5-dinitrobenzenes (X is an electron-withdrawing group) in hexamethylphosphoric triamide affords the corresponding 1-X-3-dimethylamino-5-nitrobenzenes.
• Direct Amination of 1-Substituted 3,5-Dinitrobenzenes by 1,1,1-Trimethylhydrazinium Iodide
  作者：Vladimir V. Rozhkov、Svyatoslav A. Shevelev、Ivan I. Chervin、Alexander R. Mitchell、Robert D. Schmidt

  DOI：10.1021/jo005774c

  日期：2003.3.1

  The amination of 1-X-3,5-dinitrobenzenes via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK or NaOMe in DMSO was studied. It was observed (when X = OMe, OCH2CF3, OCH2CF2CF2H, OPh) that the amination occurs regioselectively (ratio of ortho/pares-isomers is similar to9:1) and with high yield. For X = SPh or SCH2Ph, the reaction proceeded with a low yield (less than 20%), with a ratio of ortho/pares-isomers approximate to 1:1. For X = PhSO2 and 2 equiv of TMHI, a double amination occurs and 2,4-diamino-3,5dinitro-1-phenylsulfonylbenzene predominates in the mixture of isomers. Under the same conditions, 1,3,5-trinitrobenzene undergoes a double amination to yield 2,4diamino-1,3,5-trinitrobenzene. A proposed mechanism for this reaction is discussed.