1,2-bis(1,2,4-triazol-4-yl)ethane | 260251-70-5

• 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: 1,2-bis(1,2,4-triazol-4-yl)ethane
• 英文别名: btre；tr2eth；1,2-Di(4H-1,2,4-triazol-4-yl)ethane；4-[2-(1,2,4-triazol-4-yl)ethyl]-1,2,4-triazole
• CAS: 260251-70-5
• 化学式: C₆H₈N₆
• 分子量: 164.17
• InChiKey: HMPUVKXKHRDNLY-UHFFFAOYSA-N

物化性质

• 熔点：
  >260 °C(Solv: methanol (67-56-1))
• 沸点：
  409.4±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  1,2-bis(1,2,4-triazol-4-yl)ethane 、 copper(ll) bromide 以 水 为溶剂， 以55%的产率得到catena-[(μ4-1,2-bis(1,2,4-triazol-4-yl)ethane-κN1:κN2:κN1':κN2')-dibromo-dicopper(I)]
  参考文献：
  名称：

  Crystal Structure Solid-State Cross Polarization Magic Angle Spinning¹³C NMR Correlation in Luminescent d¹⁰Metal-Organic Frameworks Constructed with the 1,2-Bis(1,2,4-triazol-4-yl)ethane Ligand

  摘要：

  Hydrothermal reactions of 1,2-bis(1,2,4-triazol-4-yl)ethane (btre) with copper(II), zinc(II), and cadmium(11) salts have yielded the dinuclear complexes [Zn2Cl4(mu(2)-btre)(2)] (1) and [Zn2Br4(mu(2)-btre)(2)] (2), the one-dimensional coordination polymer (1)(infinity)[Zn(NCS)(2)(mu(2)-btre)] (3), the two-dimensional networks (2)(infinity)[Cu-2(mu(2)-Cl)(2)(mu(4)-btre)] (4), [Cu-2(mu(2)-Br)(2)(mu(4)-btre)] (5), and (2)(infinity){[Cd-6(mu(3)-OH)(2)(mu(3)-SO4)(4)(mu(4)-btre)(3)(H2O)(6)](SO4) center dot similar to 6H(2)O} (6), and the three-dimensional frameworks (3)(infinity){[Cu(mu(4)-btre)]ClO4 center dot similar to 0.25H(2)O} (7), (3)(infinity){[Zn(mu(4)-btre)(mu(2)-btre)](ClO4)2} (8), (3)(infinity){[Cd(mu(4)-btre)(mu(2)-btre)](ClO4)(2)] (9), and (3)(infinity)[Cu-2(mu(2)-CN)(2)(mu(4)-btre)] (10, 2-fold 3D interpenetrated framework). The copper-containing products 4, 5, 7, and 10 contain the metal in the +1 oxidation state, from a simultaneous redox and self-assembly reaction of the Cu(II) starting materials. The cyanide-containing framework 10 has captured the CN- ions from the oxidative btre decomposition. The perchlorate frameworks 7, 8, or 9 react in an aqueous NH4+PF6- solution with formation of the related PF6--containing frameworks. The differences in the metal-btre bridging mode (mu(2)-kappa N1:N1', mu(2)-kappa N1:N2 or mu(4)-kappa N1:N2:N1':N2') and the btre ligand symmetry can be correlated with different signal patterns in the C-13 cross polarization magic angle spinning (CPMAS) NMR spectra. Compounds 2, 4, 5 and 7 to 10 exhibit fluorescence at 403-481 nm upon excitation at 270-373 nm which is not seen in the free btre ligand.

  DOI：

  10.1021/ic802069k

文献信息

• Syntheses, structures and photocatalytic degradation of organic dyes for two isostructural copper coordination polymers involving <i>in situ</i> hydroxylation reaction
  作者：Yan-Fen Peng、Lin-Lu Qian、Jian-Gang Ding、Tian-Rui Zheng、Ya-Qian Zhang、Bao-Long Li、Hai-Yan Li

  DOI：10.1080/00958972.2018.1460664

  日期：2018.5.3

  Abstract Two copper(II) coordination polymers, [Cu2(btre)(hsuc)Cl(H2O)]·1.5H2O}n (1) and [Cu2(btre)(hsuc)Br(H2O)]·1.5H2O}n (2) (btre = 1,2-bis(1,2,4-triazol-4-yl)ethane, H3hsuc = 2-hydroxysuccinic acid), were synthesized by the hydrothermal method via in situ hydroxylation reaction with fumarate (fum), btre and CuCl2/CuBr2, and characterized by elemental analyses, IR, TG and X-ray diffraction. 1

  摘要 两种铜 (II) 配位聚合物，[Cu2(btre)(hsuc)Cl(H2O)]·1.5 }n (1) 和 [Cu2(btre)(hsuc)Br( )]·1.5 } n (2) (btre = 1,2-bis(1,2,4-triazol-4-yl)ethane, H3hsuc = 2-hydroxysuccinic acid)，通过水热法与富马酸酯（fum )、btre 和 CuCl2/CuBr2，并通过元素分析、IR、TG 和 X 射线衍射表征。图 1 和图 2 是同构的，显示了基于 [Cu2O] 二聚体的 4 连接二维网络。图1和图2在紫外光照射下对有机染料亚甲蓝和甲基橙的降解表现出良好的光催化活性。
• Metal oxide-organic frameworks (MOOFs), a new series of coordination hybrids constructed from molybdenum(vi) oxide and bitopic 1,2,4-triazole linkers
  作者：Andrey B. Lysenko、Ganna A. Senchyk、Jörg Lincke、Daniel Lässig、Andrey A. Fokin、Ekaterina D. Butova、Peter R. Schreiner、Harald Krautscheid、Konstantin V. Domasevitch

  DOI：10.1039/b922732f

  日期：——

  A series of molybdenum(VI) oxide–organic solids were prepared by hydrothermal reactions employing N-donor tectons, which combine two 1,2,4-triazol-4-yl sites separated by representative aliphatic spacers (ethylene, tr2eth; 1,3-propylene, tr2pr; trans-1,4-cyclohexanediyl, tr2cy; diamondoid 1,3-adamantanediyl, tr2ad; 1,6- and 4,9-diamantanediyls, 1,6-tr2dia and 4,9-tr2dia) and heterofunctional 5-[4-(1,2,4-triazol-4-yl)phenyl]tetrazole (trtz). In all the compounds the 1,2,4-triazol-4-yl group acts as a short-distance N1,N2-bridge between two Mo ions (Mo–N 2.36–2.50 Å). The 3D framework structure is based upon pseudo-41 helices ([Mo4O12(tr2eth)2] 1, [Mo2O6(tr2cy)] 3) or sinusoidal chains ([Mo2O6(tr2pr)] 2, [Mo2O6(tr2ad)]·6H2O 4, [Mo2O6(4,9-tr2dia)]·0.5H2O 5) of vertex-sharing MoO4N2 octahedra, while the bitopic organic ligands manifest a dual role as connectors for two adjacent octahedra and as links between separate 1D inorganic subtopologies. For linear, lengthy tectons tr2cy and 4,9-tr2dia two identical frameworks interpenetrate. In [MoO3(trtz)] 7, the 41 helices aggregate into 3D tetragonal framework (five-fold interpenetrated) by hydrogen bonding between the tetrazole groups. The 2D structure of [Mo4O12(1,6-tr2dia)]·2H2O 6 is influenced by the very bulky aliphatic portion of the ligands, which connect chains of edge-shared octahedra MoO5N (Mo–N 2.346(2), 2.456(2) Å).

  1,3-丙烯，tr2pr；反式-1,4-环己二基，tr2cy；菱形-1,3-金刚烷二基，tr2ad；1,6-和 4,9-二金刚烷二基，1,6-tr2dia 和 4,9-tr2dia）以及杂官能团 5-[4-(1,2,4-三唑-4-基)苯基]四氮唑（trtz）。在所有化合物中，1,2,4-三唑-4-基团在两个钼离子（Mo-N 2.36-2.50 Å）之间起着短距离 N1、N2 桥的作用。三维框架结构基于伪 41 螺旋（[Mo4O12(tr2eth)2] 1、[Mo2O6(tr2cy)] 3）或正弦链（[Mo2O6(tr2pr)] 2、[Mo2O6(tr2ad)]-6H2O 4、[Mo2O6(4,9-tr2dia)]-0.5H2O 5）的顶点共享 MoO4N2 八面体，而二位有机配体则表现出双重作用，既是两个相邻八面体的连接体，又是独立的一维无机子拓扑之间的纽带。对于线性长构造体 tr2cy 和 4,9-tr2dia 而言，两个相同的框架相互渗透。在[MoO3(trtz)] 7 中，41 个螺旋通过四氮唑基团之间的氢键聚合成三维四方框架（五倍互穿）。Mo4O12(1,6-tr2dia)]-2H2O 6 的二维结构受到配体中非常笨重的脂肪族部分的影响，这些配体连接了边缘共享八面体 MoO5N 链（Mo-N 2.346(2)、2.456(2) Å）。
• Crystal structures and solid-state CPMAS 13C NMR correlations in luminescent zinc(II) and cadmium(II) mixed-ligand coordination polymers constructed from 1,2-bis(1,2,4-triazol-4-yl)ethane and benzenedicarboxylate
  作者：Hesham A. Habib、Anke Hoffmann、Henning A. Höppe、Christoph Janiak

  DOI：10.1039/b812670d

  日期：——

  The hydrothermal reaction of M(NO3)2·4H2O (M = Zn and Cd) with benzene-1,4-dicarboxylic acid (H2bdc) or benzene-1,3-dicarboxylic acid (H2ip) and 1,2-bis(1,2,4-triazol-4-yl)ethane (btre) produced the mixed-ligand coordination polymers (MOFs) 3∞[Zn2(μ2-bdc)2(μ4-btre)]} (1), 3∞[Cd2(μ4-bdc)(μ4-btre)2](NO3)2·H2O} (2) and 2∞[Zn2(μ3-ip)2(μ2-btre)(H2O)2]·2H2O} (3). The compounds, characterized by single-crystal X-ray diffraction, X-ray powder diffraction, solid-state cross-polarization (CP) magic-angle-spinning (MAS) 13C NMR and thermoanalysis, feature 3D metal–organic frameworks for 1 and 2 and 2D double layers which are connected through hydrogen bonds from the aqua ligands for 3. The CPMAS 13C NMR spectra picture the symmetry-independent (unique) C atoms and the bdc/ip-to-btre ligand ratio in agreement with the crystal structures. The zinc and cadmium coordination polymers 1–3 show a strong bluish fluorescence upon excitation with UV light (the free btre ligand is non-luminescent).

  M(NO3)2·4 （M = Zn 和 Cd）与苯-1,4-二羧酸（H2bdc）或苯-1,3-二羧酸（H2ip）及1,2-二(1,2,4-三唑-4-基)乙烷（btre）在水热反应中合成了混合配体协调聚合物（MOFs）3∞[Zn2(μ2-bdc)2(μ4-btre)]} (1)、3∞[Cd2(μ4-bdc)(μ4-btre)2]( )2·H2O} (2) 和2∞[Zn2(μ3-ip)2(μ2-btre)( )2]·2 } (3)。这些化合物通过单晶 X 射线衍射、X 射线粉末衍射、固态交叉极化（CP）魔角旋转（MAS）13C NMR 和热分析进行表征。化合物1和2具有三维金属有机框架，而化合物3呈二维双层结构，通过水合配体的氢键连接。CPMAS 13C NMR 光谱显示了与晶体结构一致的对称无关（独特）C原子和bdc/ip与btre配体的比例。锌和镉协调聚合物1-3在紫外光激发下表现出强烈的泛蓝荧光（自由的btre配体不发光）。
• Crystal Structure, Magnetic Properties, and ⁵⁷Fe Mössbauer Spectroscopy of the Two-Dimensional Coordination Polymers [M(1,2-bis(1,2,4-triazol-4-yl)ethane)₂(NCS)₂] (M^II = Fe, Co)
  作者：Yann Garcia、Georges Bravic、Christine Gieck、Daniel Chasseau、Wolfgang Tremel、Philipp Gütlich

  DOI：10.1021/ic050971l

  日期：2005.12.1

  K. The surprising absence of spin-crossover behavior for this Fe(II)-1,2,4-triazole polymeric coordination compound that has been confirmed by pressure experiments up to approximately 12 kbar and by light irradiation experiments at 10 K is discussed on the basis of its structural features. Insight into the origin of the cooperative effects of the spin transition in [Fe(btr)(2)(NCS)(2)].H(2)O (btr =

  式[M（btre）（2）（NCS）（2）]的新配位聚合物（btre = 1,2-双（1,2,4-三唑-4-基）乙烷; M（II）= Fe ，Co）已经合成，并且它们的晶体结构已经通过X射线分析在293K下确定。Fe（II）化合物（C（7）H（8）FeN（7）S（2））在单斜空间群P2（1）/ n中结晶，a = 12.439（5）A，b = 8.941（2） ）A，c = 9.321（3）A，beta = 90.88（2）度，V = 1036.6（6）A（3），Z = 2，3791反射[I> 3sigma（I）]，R（F）= 0.036，wR2 = 0.123。Co（II）化合物与Fe（II）化合物同构。晶体结构由2D薄片组成，其中金属离子通过双单齿（N1，N1'）1,2,4-三唑配体连接。该结构通过两个相邻薄板之间的pi键相互作用以及S ... S相互作用而得以稳定。随温度变化的SQUID，（57）Fe
• Mixed-ligand coordination polymers from 1,2-bis(1,2,4-triazol-4-yl)ethane and benzene-1,3,5-tricarboxylate: Trinuclear nickel or zinc secondary building units for three-dimensional networks with crystal-to-crystal transformation upon dehydration
  作者：Hesham A. Habib、Joaquin Sanchiz、Christoph Janiak

  DOI：10.1039/b715812b

  日期：——

  the dehydration procedure (freeze-drying) for 1 and (heating to 280 degrees C) for allowed for a solid-state reaction with single-crystal-to-single-crystal structural transformations in obtaining the largely dehydrated products 3 infinity[Ni3(mu2-btc)2(mu4-btre)2(mu-H2O)2(H2O)2].4H2O} (2) and 3 infinity[Zn3(mu6-btc)2(mu4-btre)2]. approximately 0.67H2O} (4), respectively. In the transformation from

  M（NO3）2.6 （M = Ni和Zn）与苯1,3,5-三羧酸（H3btc）和1,2-双（1,2,4-三唑-4-基）的水热反应乙烷（btre）产生了无穷大的混合配体配位聚合物（MOFs）3 [Ni3（mu3-btc）2（mu（4）-btre）2（mu-H2O）2]。大约22 }（1）和3个无穷大[Zn3（mu4-btc）2（mu4-btre）（ ）2] .2 }（3）。这些化合物的特征在于单晶X射线衍射，X射线粉末衍射和热分析，在三维框架内具有三核二级建筑单元（SBU）。从1.9-300 K之间的磁化率测量值来看，1中的三核镍单元表现出三聚体内部以及一些弱的三聚体间反铁磁耦合，J = -13.88（8）cm（-1）。锌配位聚合物3在323nm处激发时在423nm处显示强荧光（在游离的btre配体中未观察到）。化合物3具有耐热性，直到200摄氏度（环境压力）为止，此时水