2,6-二氨基吡嗪 | 41536-80-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2,6-二氨基吡嗪
• 中文别名: 吡嗪-2,6-二胺
• 英文名称: 2,6-Diaminopyrazine
• 英文别名: 2,6-Diamino-1,4-pyrazine；2,6-pyrazinediamine；pyrazine-2,6-diamine；pyrazine-2,6-diyldiamine；Pyrazin-2,6-diyldiamin
• CAS: 41536-80-5
• 化学式: C₄H₆N₄
• mdl: MFCD09907864
• 分子量: 110.118
• InChiKey: GYRUCENCQMAGLO-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138℃
• 沸点：
  394.1±37.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  8
• 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：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温且干燥环境中存放。

反应信息

• 作为反应物：
  描述：

  2,6-二氨基吡嗪 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以69%的产率得到3,5-二溴吡嗪-2,6-二胺
  参考文献：
  名称：

  2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants

  摘要：

  芳基硼酸与2,6-二胺-3,5-二溴-1,4-吡嗪（6）的耦合反应生成了2,6-二氨基-3,5-二芳基-1,4-吡嗪（7）。7与甲基乙二醛在水相乙醇-盐酸中反应，得到了N,N"-二取代产物8，而不是预期的 bicyclic 噁唑吡嗪酮1。2,6-二[1-(乙氧基羧基)-乙基氨基]-3,5-二芳基-1,4-吡嗪8是强效的AAPH诱导亚油酸过氧化的抑制剂。

  DOI：

  10.1055/s-2001-12764
• 作为产物：
  描述：

  2,6-二溴吡嗪 在 ammonium hydroxide 作用下， 生成 2,6-二氨基吡嗪
  参考文献：
  名称：

  Syntheses in the Pyrazine Series: The Proof of the Structure and the Reactions of 2,6-Dibromopyrazine

  摘要：

  DOI：

  10.1021/ja01174a041

文献信息

• Bimodal association of a bis-1,2,3-dithiazolyl radical
  作者：Alicea A. Leitch、Courtney E. McKenzie、Richard T. Oakley、Robert W. Reed、John F. Richardson、Lenora D. Sawyer

  DOI：10.1039/b517098b

  日期：——

  The N-ethyl pyrazine-bridged bis-1,2,3-dithiazolyl radical 2 (R1 = Et) associates at room temperature as a C–C bonded σ-dimer which, on heating, converts to a laterally S–S σ-bonded structure.

  N- 乙基吡嗪键合的双-1,2,3-二噻唑基 2（R1 = Et）在室温下以 C-C 键合的σ-二聚体形式结合，加热后转变为横向的 S-S σ 键合结构。
• Hydrogen bond donor–acceptor–donor organocatalysis for conjugate addition of benzylidene barbiturates via complementary DAD–ADA hydrogen bonding
  作者：Franco King-Chi Leung、Jian-Fang Cui、Tsz-Wai Hui、Zhong-Yuan Zhou、Man-Kin Wong

  DOI：10.1039/c4ra04020a

  日期：——

  Organocatalysts featuring a hydrogen bond donor–acceptor–donor structural element catalyze conjugate addition via complementary DAD–ADA hydrogen bonding.

  含有氢键给体-受体-给体结构元素的有机催化剂，通过互补的DAD-ADA氢键作用催化共轭加成。
• 具有杀线虫活性的三氟烯烃类化合物及其制备方法和用途
  申请人：华东理工大学

  公开号：CN113527129A

  公开（公告）日：2021-10-22

  本发明涉及一种具有杀线虫活性的含三氟烯烃类化合物及其制法和用途。具体地，本发明公开了具有式(I)化合物或其光学异构体、顺反异构体或农药学上可接受的盐，及其制备方法。上述化合物具有优异的杀线虫活性。
• An Improved Synthesis of 2,6-Diamino-3,5-Dinitropyrazine-1-Oxide
  作者：Xiaofeng Zhao、Zuliang Liu

  DOI：10.3184/174751913x13718095951814

  日期：2013.7

  An improved synthesis of 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105) is described, using N-nitroso-bis-(cyanomethyl)amine as the starting material in four steps including cyclisation, acidification; nitration and N-oxidation with a total yield of 54%. The factors influencing the reaction steps are discussed.

  本文介绍了一种改进的 2,6-二氨基-3,5-二硝基吡嗪-1-氧化物（LLM-105）的合成方法，该方法以 N-亚硝基-双（氰甲基）胺为起始原料，通过环化、酸化、硝化和 N-氧化等四个步骤合成，总产率为 54%。对影响反应步骤的因素进行了讨论。
• An Alternating π-Stacked Bisdithiazolyl Radical Conductor
  作者：Alicea A. Leitch、Robert W. Reed、Craig M. Robertson、James F. Britten、Xueyang Yu、Richard A. Secco、Richard T. Oakley

  DOI：10.1021/ja071218p

  日期：2007.6.1

  A general synthetic route to the resonance-stabilized pyrazine-bridged bisdithiazolyl framework, involving the reductive deprotection of 2,6-diaminopyrazine-bisthiocyanate and cyclization with thionyl chloride, has been developed. An N-methyl bisdithiazolyl radical, 4-methyl-4H-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyrazin-3-yl, has been prepared and characterized in solution by electron paramagnetic resonance spectroscopy and cyclic voltammetry. Its crystal structure has been determined at several temperatures. At 295 K, the structure belongs to the space group Cmca and consists of evenly spaced radicals pi-stacked in an alternating ABABAB fashion along the x-direction. At 123 K, the space group symmetry is lowered by loss of C-centering to Pccn, so that the radicals are no longer evenly spaced along the pi-stack. At 88 K, a further lowering of space group symmetry to P2(1)/c is observed. Extended Huckel Theory band structure calculations indicate a progressive opening of a band gap at the Fermi level in the low-temperature structures. Magnetic susceptibility measurements over the range 4-300 K reveal essentially diamagnetic behavior below 120 K. Variable-temperature single-crystal conductivity (sigma) measurements indicate that the conductivity is activated, even at room temperature, with a room-temperature value sigma(RT) = 0.001 S cm(-1) and a thermal activation energy E-act = 0.19 eV. Under an applied pressure of 5 GPa, sigma(RT) is increased by 3 orders of magnitude, but the conductivity remains activated, with E-act being lowered to 0.11 eV at 5.5 GPa.