3,4-dibromo-5-isothiazolecarbonitrile | 81910-94-3

• 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: 3,4-dibromo-5-isothiazolecarbonitrile
• 英文别名: 3,4-dibromoisothiazole-5-carbonitrile；3,4-dibromo-5-cyanoisothiazole；3,4-Dibromo-1,2-thiazole-5-carbonitrile
• CAS: 81910-94-3
• 化学式: C₄Br₂N₂S
• 分子量: 267.931
• InChiKey: ACLFQCHSHNIUKE-UHFFFAOYSA-N

物化性质

• 熔点：
  107.5-108.5 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  213.6±40.0 °C(Predicted)
• 密度：
  2.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 3,4-dibromo-5-isothiazolecarbonitrile 以 甲苯 为溶剂， 反应 2.0h， 以55%的产率得到4-bromo-3-(pyrrolidin-1-yl)isothiazole-5-carbonitrile
  参考文献：
  名称：

  Reactions of selected 3-bromoisothiazole-5-carbonitriles with the secondary dialkylamines pyrrolidine and morpholine

  摘要：

  Readily available 3-bromoisothiazole-5-carbonitriles bearing various C-4 substituents [H, CO2R C N and halogen (CI or Br)], react with either pyrrolidine or morpholine to give, in most cases, the 3-amino-substituted derivatives in high yields. The reaction of 3-bromoisothiazole-4,5-dicarbonitrile, however, varied with the nucleophilicity of the dialkylamine: pyrrolidine led to cleavage of the isothiazole ring to give 2-[di(pyrrolidin-1-yl)methylene]malononitrile while morpholine led to the expected 3-(morpholin-4-yl)isothiazole-4,5-dicarbonitrile. By comparison, 3-chloroisothiazole-4,5-dicarbonitrile reacted with pyrrolidine to give surprisingly, 3-chloro-5-(pyrrolidin-1-yl)isothiazole-4-carbonitrile as the major product, while with morpholine the major product was the expected 3-(morpholin-4-yl)isothiazole-4,5-dicarbonitrile. The mechanisms of the transformations are discussed, together with rationalization for the formation of side products. Furthermore, the hydrolytic decarboxylation of methyl and ethyl esters of 3-dialkylaminoisothiazoles using both conventional heating and microwave irradiation is reported. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.012
• 作为产物：
  描述：

  丁烷-1,4-二胺 在 二氧化硫 、 氢溴酸 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以35%的产率得到3,4-dibromo-5-isothiazolecarbonitrile
  参考文献：
  名称：

  Zborovskii, Yu. L.; Smirnov-Zamkov, I. V.; Staninets, V. I., Journal of Organic Chemistry USSR (English Translation), 1984, p. 1617 - 1625

  摘要：

  DOI：

文献信息

• Ring transformation of (4-chloro-5H-1,2,3-dithiazol-5-ylidene)acetonitriles to 3-haloisothiazole-5-carbonitriles
  作者：Andreas S. Kalogirou、Irene C. Christoforou、Heraklidia A. Ioannidou、Manolis J. Manos、Panayiotis A. Koutentis

  DOI：10.1039/c3ra47261b

  日期：——

  Improved conditions for the ring transformation of 1,2,3-dithiazoles into isothiazole-5-carbonitriles are presented together with mechanistic rationale.

  提供了改进的条件，用于将1,2,3-二噻唑转化为异噻唑-5-碳腈，并附带机理解释。
• Zborovskii, Yu. L.; Smirnov-Zamkov, I. V.; Staninets, V. I., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 586
  作者：Zborovskii, Yu. L.、Smirnov-Zamkov, I. V.、Staninets, V. I.

  DOI：——

  日期：——
• ZBOROVSKIJ, YU. L.;SMIRNOV-ZAMKOV, I. V.;STANINETS, V. I., ZH. ORGAN. XIMII, 1982, 18, N 3, 675-676
  作者：ZBOROVSKIJ, YU. L.、SMIRNOV-ZAMKOV, I. V.、STANINETS, V. I.

  DOI：——

  日期：——
• ZBOROVSKIJ, YU. L.;SMIRNO-ZAMKOV, I. V.;STANINETS, V. I., ZH. ORGAN. XIMII, 1984, 20, N 8, 1774-1784
  作者：ZBOROVSKIJ, YU. L.、SMIRNO-ZAMKOV, I. V.、STANINETS, V. I.

  DOI：——

  日期：——
• Zborovskii, Yu. L.; Smirnov-Zamkov, I. V.; Staninets, V. I., Journal of Organic Chemistry USSR (English Translation), 1984, p. 1617 - 1625
  作者：Zborovskii, Yu. L.、Smirnov-Zamkov, I. V.、Staninets, V. I.

  DOI：——

  日期：——