4,6-dimethyl-2-hydroxypyrimidine hydrobromide | 66653-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,6-dimethyl-2-hydroxypyrimidine hydrobromide
• 英文别名: 4,6-dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium bromide；4,6-dimethyl-1H-pyrimidin-2-one; hydrobromide；4,6-Dimethyl-1H-pyrimidin-2-on; Hydrobromid；4,6-Dimethyl-2-pyrimidonium bromide；4,6-dimethyl-1H-pyrimidin-3-ium-2-one;bromide
• CAS: 66653-17-6
• 化学式: BrH*C₆H₈N₂O
• 分子量: 205.054
• InChiKey: CDXHOEBDSYPTLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.75
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-(ω-bromobutylthio)-4,6-dimethylpyrimidine 、 水 以98%的产率得到
  参考文献：
  名称：

  MIXAJLOV, A. S.;PASHKUROV, N. G.;REZNIK, V. S., IZV. AN CCCP. CEP. XIM., 1982, N 1, 155-161

  摘要：

  DOI：

文献信息

• Impact of the anion and chalcogen on the crystal structure and properties of 4,6-dimethyl-2-pyrimido(thio)nium halides
  作者：Andrzej Okuniewski、Damian Rosiak、Jarosław Chojnacki

  DOI：10.1107/s2053229620005525

  日期：2020.5.1

  By the reaction of urea or thiourea, acetylacetone and hydrogen halide (HF, HBr or HI), we have obtained seven new 4,6-dimethyl-2-pyrimido(thio)nium salts, which were characterized by single-crystal X-ray diffraction, namely, 4,6-dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium bifluoride, C₆H₉N₂O⁺·HF₂ ⁻ or (dmpH)F₂H, 4,6-dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium bromide, C₆H₉N₂O⁺·Br⁻ or (dmpH)Br, 4,6-dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium iodide, C₆H₉N₂O⁺·I⁻ or (dmpH)I, 4,6-dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium iodide–urea (1/1), C₆H₉N₂O⁺·I⁻·CH₄N₂O or (dmpH)I·ur, 4,6-dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium bifluoride–thiourea (1/1), C₆H₉N₂S⁺·HF₂ ⁻·CH₄N₂S or (dmptH)F₂H·tu, 4,6-dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium bromide, C₆H₉N₂S⁺·Br⁻ or (dmptH)Br, and 4,6-dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium iodide, C₆H₉N₂S⁺·I⁻ or (dmptH)I. Three HCl derivatives were described previously in the literature, namely, 4,6-dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium chloride, (dmpH)Cl, 4,6-dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium chloride monohydrate, (dmptH)Cl·H₂O, and 4,6-dimethyl-2-sulfanylidene-2,3-dihydropyrimidin-1-ium chloride–thiourea (1/1), (dmptH)Cl·tu. Structural analysis shows that in 9 out of 10 of these compounds, the ions form one-dimensional chains or ribbons stabilized by hydrogen bonds. Only in one compound are parallel planes present. In all the structures, there are charge-assisted N⁺—H...X ⁻ hydrogen bonds, as well as weaker C_Ar ⁺—H...X ⁻ and π⁺...X ⁻ interactions. The structures can be divided into five types according to their hydrogen-bond patterns. All the compounds undergo thermal decomposition at relatively high temperatures (150–300 °C) without melting. Four oxopyrimidinium salts containing a π⁺...X ⁻...π⁺ sandwich-like structural motif exhibit luminescent properties.

  通过尿素或硫脲、乙酰丙酮和卤化氢（HF、HBr 或 HI）的反应，我们得到了七种新的 4,6-二甲基-2-嘧啶（硫）鎓盐，并通过单晶 X 射线衍射对其进行了表征，它们是：4,6-二甲基-2-氧代-2,3-二氢嘧啶-1-鎓双氟化物 C6H9N2O+-HF2 - 或 (dmpH)F2H；4,6-二甲基-2-氧代-2,3-二氢嘧啶-1-鎓溴化物， +-Br- 或 (dmpH)Br；4,6-二甲基-2-氧代-2,3-二氢嘧啶-1-鎓碘化物， +-I- 或 (dmpH)I；4、6-二甲基-2-氧代-2,3-二氢嘧啶-1-鎓碘化脲(1/1)， +-I--CH4N2O 或 (dmpH)I-ur, 4,6-二甲基-2-硫代-2,3-二氢嘧啶-1-鎓双氟化硫脲(1/1)，C6H9N2S+-HF2 --CH4N2S或(dmptH) -tu、4,6-二甲基-2-亚硫酰基-2,3-二氢嘧啶-1-鎓溴化物， +-Br-或(dmptH)Br，以及4,6-二甲基-2-亚硫酰基-2,3-二氢嘧啶-1-鎓碘化物， +-I-或(dmptH)I。以前的文献中介绍过三种盐酸衍生物，即 4,6-二甲基-2-氧代-2,3-二氢嘧啶-1-鎓氯化物 (dmpH)Cl、4,6-二甲基-2-亚硫酰-2、(dmptH)Cl-H2O，以及 4,6-二甲基-2-亚硫酰-2,3-二氢嘧啶-1-鎓氯化物 (1/1)，(dmptH)Cl-tu。结构分析表明，在这 10 个化合物中有 9 个中，离子形成了由氢键稳定的一维链或带。只有一种化合物存在平行平面。在所有结构中，都存在电荷辅助的 N+-H...X - 氢键，以及较弱的 CAr +-H...X - 和 π+...X - 相互作用。根据氢键模式，这些结构可分为五种类型。所有化合物都在相对较高的温度（150-300 ℃）下发生热分解而不熔化。四种含有 π+...X -...π+"三明治 "状结构基团的四种嘧啶氧化盐具有发光特性。
• Reaction of 2-(?-bromoalkylthio)-4,6-dimethylpyrimidines with some nucleophilic reagents
  作者：A. S. Mikhailov、N. G. Pashkurov、V. S. Reznik

  DOI：10.1007/bf00954426

  日期：1982.1