4-溴-1-[(4-溴吡唑-1-基)甲基]吡唑 | 86111-61-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 4-溴-1-[(4-溴吡唑-1-基)甲基]吡唑
• 英文名称: dibromo-4,4' methylene-1,1' dipyrazole
• 英文别名: bis(4-bromo-1H-pyrazol-1-yl)methane；bis(4-bromopyrazol-1-yl)methane；bis(4-bromopyrazolyl)methane；1H-Pyrazole, 1,1'-methylenebis(4-bromo-；4-bromo-1-[(4-bromopyrazol-1-yl)methyl]pyrazole
• CAS: 86111-61-7
• 化学式: C₇H₆Br₂N₄
• 分子量: 305.959
• InChiKey: SSYOJYMXWXULTA-UHFFFAOYSA-N

物化性质

• 沸点：
  404.8±30.0 °C(Predicted)
• 密度：
  2.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-溴-1-[(4-溴吡唑-1-基)甲基]吡唑 在 盐酸 、 叔丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.67h， 生成 bis(4-dihydroxyboryl-5-t-butylamido-1H-pyrazol-1-yl)methane
  参考文献：
  名称：

  Formation of dilithiated bis-(1H-pyrazol-1-yl)alkanes and their application in the synthesis of diboronic acids

  摘要：

  Bis-(1H-pyrazol-1-yl)alkanes were deprotonated at the pyrazole 5-positions on treatment with LDA in THF at low temperature. These dianions reacted with tert-butylisocyanate as the electrophile to install a tert-butylamide group at the pyrazole 5-position. The obtained amides were next converted into the respective diboronic acids by Br-Li exchange with t-BuLi in THF at low temperature, followed by the use of triethyl borate as the electrophile. The X-ray analysis of the obtained diboronic acids revealed the presence of a variety of structural motifs, which stabilize the structure by hydrogen bond formation. The stabilization pattern differs greatly with a minor modification of the linker connecting the pyrazole rings. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.007
• 作为产物：
  描述：

  1-(1-吡唑甲基)吡唑 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以90%的产率得到4-溴-1-[(4-溴吡唑-1-基)甲基]吡唑
  参考文献：
  名称：

  Claramunt, Rosa Maria; Hernandez, Helena; Elguero, Jose, Bulletin de la Societe Chimique de France, 1983, vol. 2, # 1-2, p. 5 - 10

  摘要：

  DOI：

文献信息

• Synthesis, structures and electrochemical properties of VIB carbonyl complexes containing bis(4-halopyrazol-1-yl)alkanes
  作者：Liang-Fu Tang、Zhi-Hong Wang、Yu-Ming Xu、Ji-Tao Wang、Hong-Gen Wang、Xin-Kan Yao

  DOI：10.1016/s0277-5387(99)00142-4

  日期：1999.7

  Abstract Bis(4-halopyrazol-1-yl)alkanes (1=bis(4-bromopyrazol-1-yl)methane CH2(4-BrPz)2, 2=bis(3,5-dimethyl-4-bromopyrazol-1-yl)methane CH2(3,5-Me2-4-BrPz)2, 3=bis(4-chloropyrazol-1-yl)methane CH2(4-ClPz)2, 4=bis(3,5-dimethyl-4-chloro-pyrazol-1-yl)methane CH2(3,5-Me2-4-ClPz)2) have been synthesized by the reaction of bis(pyrazol-1-yl)methane or bis(3,5-dimethylpyrazol-1-yl)methane with Br2 or SO2Cl2

  摘要双（4-卤吡唑-1-基）烷烃（1 =双（4-溴吡唑-1-基）甲烷CH2（4-BrPz）2，2 =双（3,5-二甲基-4-溴吡唑-1- yl）甲烷CH2（3,5-Me2-4-BrPz）2，3 =双（4-氯吡唑-1-基）甲烷CH2（4-ClPz）2，4 =双（3,5-二甲基-4-氯吡唑-1-基甲烷CH2（3,5-Me2-4-ClPz）2）是通过双（吡唑-1-基）甲烷或双（3,5-二甲基吡唑-1-基）反应合成的甲烷）与Br2或SO2Cl2。这些配体与M（CO）6（M = Cr，Mo，W）反应，以合理的产率生成双（4-卤吡唑-1-基）甲烷四羰基铬（0），钼（0）和钨（0）配合物。对于钨配合物，所有新化合物均已通过元素分析，IR，1H NMR和13C NMR进行了表征。通过循环伏安图研究的这些配合物的电化学性质表明，每种化合物均显示出一个与单电子氧化相对应的可逆或准可逆对。X射线晶体学测定的CH2（3
• Synthesis and characterization of bidentate organotin Lewis acid derivatives containing bis(pyrazol-1-yl)alkanes: X-ray crystal structure of PhBr2(L)SnCH2SnPhBr2 (L=bis(4-chloropyrazol-1-yl)methane)
  作者：Zhi-Hong Wang、Liang-Fu Tang、Wen-Li Jia、Ji-Tao Wang、Hong-Gen Wang

  DOI：10.1016/s0277-5387(02)00863-x

  日期：2002.4

  The reaction between bis(dibromophenylstannyl)methane, [CH2(SnPhBr2)(2)], with bis(pyrazol-1-yl)alkanes, [(CH2)(n)Pz(2)] (n = 1 or 2; Pz = substituted pyrazole) in a 1: 1 or 1:2 ratio yields only 1: 1 adducts of PhBr2[(CH2)(n)Pz(2)]SnCH2SnPhBr2, which have been confirmed by elemental analysis, H-1 NMR and IR spectroscopy. The electronic and steric characteristics of substituents on the pyrazole rings markedly influence the donating ability of bis(pyrazol-1-yl)alkanes to the bidentate organotin Lewis acid acceptor. The investigations on the reaction of the adducts with DMSO and NMR spectra of the adducts show the weak interactions between ligands and the bidentate organotin Lewis acid acceptor. X-Ray analysis of PhBr2(CH2(4-ClPZ)(2))SnCH2SnPhBr2 showed that bis(4-chloropyrazol-1-yl)methane acts as a chelating bidentate ligand to only one tin atom. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Zinc(II), cadmium(II) and mercury(II) derivatives of bis(4-halopyrazol-1-yl)alkanes: synthesis, spectroscopic characterization and behaviour in solution
  作者：C. Pettinari、A. Lorenzotti、M. Pellei、C. Santini

  DOI：10.1016/s0277-5387(97)00089-2

  日期：1997.1

  The interaction between various bis(4-halopyrazol-1-yl)alkanes L (L* = bis(3,5-dimethyl-4-chloropyrazol-1 -yl)methane, L# = bis(4-bromopyrazol-1-yl)methane, L degrees = bis(4-chloropyrazol-1-yl)methane) and zinc(II), cadmium(II) and mercury(II) accepters gave 1:1 [LMX2] (L = L*, M = Zn, X = Cl, Br, I, NO3 or CF3CO2; L = L*, M = Cd, X = Cl Or Br; L I L*, M = Hg, X = Cl, Br or I; L = L#, Fvl = Zn, X = Cl, Br, I or NO,; L = L#, M = Cd, X = Cl, Br, I or NO3; L = L#, M = Hg, X = Cl or Br; L = L#, M = Zn, X = Cl, M = Cd, X = I, M = Hg, X = Br), 3:2 [(L*)(3)(Zn(CF3SO3)(2)}(2)].3H(2)O and [(L*)(3)(Cd(NO3)(2)}(2)].2H(2)O, 2: 1 [L,M]X, (L = L*, M = Zn or Cd, X = ClO4 or BF4; L = L*, M = Hg, X - ClO4; L = L#, M = Zn, X = ClO4 or CF3SO3, M = Cd, X = ClO4 or BF4; L degrees = L*, M = Cd, X = BF4) and finally 3:1 [(L#)(3)Zn](BF4)(2) adducts; these derivatives have been characterized through elemental analyses, spectral data (IR, H-1 and C-13 NMR in the case of the sufficiently soluble derivatives), conductivities and molecular weight measurements. Comparison is made with the results obtained with other bis(pyrazol-1-yl)alkanes. (C) 1997 Elsevier Science Ltd.
• Rhodium(I) complexes with bis(pyrazolyl)methane ligands. Crystal structure of [Rh(COD)(CH2(Pz)2)]ClO4· C2H4Cl2
  作者：L.A. Oro、M. Esteban、R.M. Claramunt、J. Elguero、C. Foces-Foces、F.H. Cano

  DOI：10.1016/0022-328x(84)80606-3

  日期：1984.11
• CLARAMUNT, R. M.;HERNANDEZ, H.;ELGUERO, J.;JULIA, S., BULL. SOC. CHIM. FRANCE, 1983, N 1-2, 5-10
  作者：CLARAMUNT, R. M.、HERNANDEZ, H.、ELGUERO, J.、JULIA, S.

  DOI：——

  日期：——