N-(2-hydroxyethyl)dithiocarbamic acid | 59333-68-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-hydroxyethyl)dithiocarbamic acid
• 英文别名: Carbamodithioic acid, (2-hydroxyethyl)-；2-hydroxyethylcarbamodithioic acid
• CAS: 59333-68-5
• 化学式: C₃H₇NOS₂
• mdl: MFCD19218573
• 分子量: 137.227
• InChiKey: MMLBEXXDOLIGCR-UHFFFAOYSA-N

物化性质

• 沸点：
  241.7±42.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  65.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)dithiocarbamic acid 在 sodium monochloroacetic acid 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 4-(2-hydroxyethyl)-thiosemicarbazide
  参考文献：
  名称：

  微波辐射下无溶剂合成吲哚基缩氨基硫脲

  摘要：

  开发了一种快速、高效且环保的方法，用于在微波辅助无溶剂条件下以氧化铝为固体载体合成吲哚-3-甲醛缩氨基硫脲。与常规加热方法相比，该方法得到的目标产物收率良好。

  DOI：

  10.3184/030823410x12628833270368
• 作为产物：
  描述：

  二硫化碳 、 C.I.酸性橙108 在 氨 作用下， 以 乙醇 、 水 为溶剂， 生成 N-(2-hydroxyethyl)dithiocarbamic acid
  参考文献：
  名称：

  微波辐射下无溶剂合成吲哚基缩氨基硫脲

  摘要：

  开发了一种快速、高效且环保的方法，用于在微波辅助无溶剂条件下以氧化铝为固体载体合成吲哚-3-甲醛缩氨基硫脲。与常规加热方法相比，该方法得到的目标产物收率良好。

  DOI：

  10.3184/030823410x12628833270368

文献信息

• Preparation of novel metal dithiocarbamate complexes containing ω-OH group. Stabilization effect of the OH group on the HNCS2-Mt linkage
  作者：Ryoki Nomura、Satoru Fujii、Akihisa Takabe、Haruo Matsuda

  DOI：10.1016/s0277-5387(00)86410-4

  日期：1989.1

  Abstract The direct condensation between metal oxide powders (Zn II , In III , Sb III and Bi III ) and dithiocarbamic acids, prepared by the reaction of ethanolamine or 1,3-propanolamine with CS 2 , gave corresponding metal dithiocarbamate complexes in good yields. Although antimony and bismuth dithiocarbamates decomposed up to 80°C to give elimination products such as oxazolidine-2-thione, thiazolidine-2-thione

  摘要乙醇胺或1,3-丙醇胺与CS 2反应制得的金属氧化物粉末（Zn II，In III，Sb III和Bi III）与二硫代氨基甲酸直接缩合，得到了相应的金属二硫代氨基甲酸酯配合物。尽管二硫代氨基甲酸锑和铋在高达80°C的温度下分解，得到消除产物，如恶唑烷-2-硫酮，噻唑烷-2-硫酮或双（3-羟丙基）硫脲，但在苯中于80℃加热后可回收锌和铟衍生物。保持6小时。在诸如Bu 2 SnO，BuSnO 2 H和Ph 3 SbO的有机金属氧化物与二硫代氨基甲酸的反应中，即使在20℃下也直接获得了消除产物。
• Synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave
  作者：Zhi Chuan Shi、Zhi Gang Zhao、Xing Li Liu、Yu Chen

  DOI：10.1016/j.cclet.2010.10.020

  日期：2011.4

  An efficient and simple method for synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave has been developed. Its main advantages are short reaction times, good conversions and the environmentally friendly nature of the process. The preliminary results indicate that some of these compounds possess inhibitory effects against E. coli. (C) 2010 Zhi Gang Zhao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Mechanisms of Acid Decomposition of Dithiocarbamates. 1. Alkyl Dithiocarbamates
  作者：Eduardo Humeres、Nito A. Debacher、M. Marta de S. Sierra、José Dimas Franco、Aldo Schutz

  DOI：10.1021/jo971869b

  日期：1998.3.1

  The acid decomposition of some substituted methyldithiocarbamates was studied in water at 25 degrees C in the range of H-0 -5 and pH 5. The pH-rate profiles showed a bell-shaped curve from which were calculated the acid dissociation constants of the free and conjugate acid species and the specific acid catalysis rate constants k(H). The Bronsted plot of k(H) vs pK(N), the dissociation constant of the conjugate acid of the parent amine, suggests that the acid cleavage occurs through two mechanisms that depend on the pK(N). The plot presents a convex upward curve with a maximum at pk(N) 9.2, which is consistent with the cleavage of the dithiocarbamate anion through a zwitterion intermediate and two transition states. For pk(N) < 9.2, the N-protonation is slower than the C-N bond breakdown. Inverse SIE showed that the zwitterion is formed through a late transition state. At pK(N) > 9.2, the C-N band breakdown is the slowest step, and according to the inverse SIE, the transition state changes rapidly with the increase of PKN to a late transition state. The plot shows a minimum at pK(N) similar to 10, indicating that a new mechanism emerges at higher values, and it is postulated that it represents a path of intramolecular S to N proton-transfer concerted with the C-N bond breakdown. The thiocarbonyl group acts as a powerful electron-withdrawing group, decreasing the basicity of the nitrogen of the parent amine by 14.1 pK units.
• Solvent-Free Synthesis of Indole-Based Thiosemicarbazones under Microwave Irradiation
  作者：Lingling Liu、Jie Yang、Zhigang Zhao、Peiyu Shi、Xingli Liu

  DOI：10.3184/030823410x12628833270368

  日期：2010.1

  A rapid, efficient and environmentally friendly methodology has been developed for the synthesis of indole-3-carboxaldehyde thiosemicarbazones by using aluminum oxide as the solid support under microwave assisted solvent-free conditions. Compared with the conventional heating method, this method gave the target products in good yield.

  开发了一种快速、高效且环保的方法，用于在微波辅助无溶剂条件下以氧化铝为固体载体合成吲哚-3-甲醛缩氨基硫脲。与常规加热方法相比，该方法得到的目标产物收率良好。