2-thiocyanatopyrimidine | 89283-87-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-thiocyanatopyrimidine
• 英文别名: Pyrimidin-2-yl thiocyanate
• CAS: 89283-87-4
• 化学式: C₅H₃N₃S
• mdl: MFCD03426917
• 分子量: 137.165
• InChiKey: RTSBUFRXTFPHEH-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  308.5±25.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2-thiocyanatopyrimidine 在 sodium azide 、 zinc(II) chloride 作用下， 以 异丙醇 为溶剂， 以84 %的产率得到2-((1H-tetrazol-5-yl)thio)pyrimidine
  参考文献：
  名称：

  使用六氰基铁酸盐作为无毒氰化物源合成有机硫氰酸盐的互补机械化学和双相方法

  摘要：

  在此，我们描述了两种互补的方法来制备各种有机硫氰酸盐，这些有机硫氰酸盐价格低廉、可靠并遵循可持续化学的原则，从市售的硫醇或二硫化物开始。此外，还展示了这种温和方法在 psammaplin B 的首次全合成中的应用。氰化物源使用无毒且廉价的铁氰化物，可以通过机械化学、无溶剂方法或双相溶剂系统激活，从而更容易进行后处理。总共展示了 27 个示例，具有高达定量的产量。

  DOI：

  10.1039/d2ob02216h
• 作为产物：
  描述：

  氯化氰 、 sodium pyrimidine-2-thiolate 以100%的产率得到2-thiocyanatopyrimidine
  参考文献：
  名称：

  Quantitative Gas-Solid Reactions with ClCN and BrCN: Synthesis of Cyanamides, Cyanates, Thiocyanates, and Their Derivatives

  摘要：

  Gas-solid reaction techniques allow quantitative cyanations with ClCN and BrCN. Three primary and four secondary cyanamides, a cyanimide, four cyanates, and four thiocyanates were all prepared as solids in 100% yield from solid anilines, benzimidazoles, imides, phenolates, and thiolates, respectively. Intramolecular solid-state reactions of cyanated o-aminophenol and of cyanated hydrazides gave heterocyclic compounds. When comparable reactions were performed in solution the reported product yields were considerably less than 100 % in all cases. The reasons for the success of the environmentally benign solid-state syntheses are discussed in terms of phase rebuilding, phase transformation, and crystal disintegration. Atomic force microscopy (AFM) of selected systems indicates the occurrence of long-range molecular movements which are governed by the crystal packing. This is evident from the obvious correlations between the molecular movements and the known crystal packing data, A new type of geometric surface feature, a rectangular and a rhombic depression which resembles a swimming-pool basin, was found in the cyanation of o-aminophenol and benzohydrazide.

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2467::aid-chem2467>3.0.co;2-d

文献信息

• General and Practical Formation of Thiocyanates from Thiols
  作者：Reto Frei、Thibaut Courant、Matthew D. Wodrich、Jerome Waser

  DOI：10.1002/chem.201406171

  日期：2015.2.2

  A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational

  描述了一种使用氰基苯并齐多醇（on）高价碘试剂氰化硫醇和二硫化物的新方法。脂肪族和芳香族硫氰酸酯都可以在室温下以几分钟的高收率获得，其起始源是多种具有高化学选择性的硫醇。也可以将二硫化物完全转化为硫氰酸酯。初步的计算研究表明，硫氰酸根阴离子或自由基的氰化反应具有低能的一致过渡态。发达的硫氰酸酯合成方法在合成化学，化学生物学和材料科学中具有广泛的应用潜力。
• A Diheteroatom Fluoroalkylation Reagent for Preparation of S- and N-Containing Fluoroalkyl Compounds and Sulfonic Acid Polymer
  作者：Jingwen Dai、Zili Li、Taisheng Wang、Wei Bai、Ruke Bai

  DOI：10.1021/acs.orglett.7b00347

  日期：2017.3.17

  The first stable diheteroatom fluoroalkylation reagent, 2-((2-azido-1-chloro-1,2,2-trifluoroethyl)thio)pyrimidine (ACTP), has been prepared by a novel method. By using this reagent, various fluorinated thioethers and sulfones have been successfully prepared. The dearylation and dearylation–oxidation of fluoroalkyl 2-pyrimidyl sulfone in one-pot reaction were investigated systematically, and the results

  第一种稳定的二杂原子氟烷基化试剂2-（（（2-叠氮基-1-氯-1,2,2-三氟乙基）硫基）嘧啶（ACTP），已经通过新型方法制备。通过使用该试剂，已经成功地制备了各种氟化硫醚和砜。系统地研究了一锅反应中氟烷基2-嘧啶砜的脱芳基和脱芳基氧化反应，结果表明氟烷基亚磺酸盐和磺酸盐均可以高收率获得。另外，ACTP被证明可用于制备氟化磺酸质子交换膜。
• Electrophilic Cyanations. I. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide
  作者：Akira Miyashita、Izuru Nagasaki、Akiko Kawano、Yumiko Suzuki、Ken-ichi Iwamoto、Takeo Higashino

  DOI：10.3987/com-97-7740

  日期：——

  Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).
• 2-Cyanopyridazin-3(2H)-ones: effective and chemoselective electrophilic cyanating agents
  作者：Jeum-Jong Kim、Deok-Heon Kweon、Su-Dong Cho、Ho-Kyun Kim、Eun-Young Jung、Sang-Gyeong Lee、J.R. Falck、Yong-Jin Yoon

  DOI：10.1016/j.tet.2005.03.138

  日期：2005.6

  2-Cyanopyridazin-3(2H)-ones are novel, effective, selective and electrophilic cyanating agents. A variety of amino, thiol and carbon nucleophiles are chemoselectively N-, S- or C-cyanated in excellent yield using 2-cyanopyridanzin-3(2H)-ones in water or tetrahydrofuran. (c) 2005 Elsevier Ltd. All rights reserved.
• Nagasaki, Izuru; Matsumoto, Miyuki; Yamashita, Masanori, Heterocycles, 1999, vol. 51, # 5, p. 1015 - 1024
  作者：Nagasaki, Izuru、Matsumoto, Miyuki、Yamashita, Masanori、Miyashita, Akira

  DOI：——

  日期：——

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