3,4-dibromo-5-phenyl-1H-pyrazole | 5932-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,4-dibromo-5-phenyl-1H-pyrazole
• 英文别名: 3(5),4-Dibrom-5(3)-phenyl-pyrazol；3,4-dibromo-5-phenyl-1(2)H-pyrazole；3,4-dibromo-5-phenylpyrazole；4,5-dibromo-3-phenyl-1H-pyrazole
• CAS: 5932-21-8
• 化学式: C₉H₆Br₂N₂
• 分子量: 301.968
• InChiKey: ZUQRSQIJYIJBAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dibromo-5-phenyl-1H-pyrazole 生成 4,5-dibromo-N,N,α-trimethyl-3-phenylpyrazole-1-acetamide 、 3,4-dibromo-N,N,α-trimethyl-5-phenylpyrazole-1-acetamide
  参考文献：
  名称：

  Pyrazole amides

  摘要：

  本发明公开了取代吡唑基的酰胺和硫代酰胺，其在α或β位置上取代，可用作除草剂。

  公开号：

  US04072498A1
• 作为产物：
  描述：

  3-苯基吡唑 在 sodium hydroxide 、 溴 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以83%的产率得到3,4-dibromo-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  Structure and tautomerism of 4-bromo substituted 1H-pyrazoles

  摘要：

  The tautomerism in the solid state and in solution of five 4-bromo-1H-pyrazoles has been studied by multinuclear magnetic resonance spectroscopy and, for one of them, by X-ray crystallography (3,4-dibromo-5-phenyl-1H-pyrazole). When there is a bromine atom at position 3(5), in all cases, the tautomer present in the solid state is the 3-bromo one. In solution, the same tautomer is the major one. DFT calculations justify the predominance of 3-bromo tautomers over 5-bromo ones and provide some useful chemical shifts obtained through GIAO calculations. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.007

文献信息

• Unusual Polybrominated Polypyrazolylborates and Their Copper(I) Complexes:  Synthesis, Characterization, and Catalytic Activity
  作者：Glen P. A. Yap、Fernando Jove、Juan Urbano、Eleuterio Alvarez、Swiatoslaw Trofimenko、M. Mar Díaz-Requejo、Pedro J. Pérez

  DOI：10.1021/ic061714z

  日期：2007.2.1

  Five new homoscorpionate ligands were prepared and structurally characterized as their Tl complexes, three of which, Tl[Tp(Br,Ph,Br)] (1) (Tp = hydrotris(pyrazolyl)borate, Tl[Tp(Br,p-Tol,Br)] (2), and Tl[Tp(Br,p-ClPh,Br)] (3), are unique in being the first examples of an "atypical" B-N bond to the most sterically hindered pyrazole nitrogen. They contain bromine atoms on the central and outer carbons of the pyrazole ring, with all aryl substituents in the 5-position of the ligand, forming a protective pocket around the B-H bond. These complexes display a rather high B-H stretch frequency (above 2 600 cm(-1)) in the IR region. Two other ligands, Tl[Tp(p-ClPh,4Br)] (4) and Tl[Tp(Ph,Me,Br)] (5), containing no outer bromine substituents, have normal B-N bonding to the least-hindered nitrogen. These new ligands have been employed to prepare the series of complexes Tp(x)Cu(NCMe) (6-10), for which X-ray studies of two of them (7 and 10) have shown that the atypical or normal geometry of the ligands is maintained when complexed to the copper center. The new complexes have also been tested as the catalysts in carbene and nitrene transfer reactions providing moderate to high yields in the expected products.
• US4072498A
  申请人：——

  公开号：US4072498A

  公开（公告）日：1978-02-07
• Pyrazole amides
  申请人：The Upjohn Company

  公开号：US04072498A1

  公开（公告）日：1978-02-07

  The present invention discloses amides and thioamides substituted in the .alpha. or .beta. position with substituted pyrazoles which are useful as herbicides.

  本发明公开了取代吡唑基的酰胺和硫代酰胺，其在α或β位置上取代，可用作除草剂。
• Structure and tautomerism of 4-bromo substituted 1H-pyrazoles
  作者：Swiatoslav Trofimenko、Glenn P.A. Yap、Fernando A. Jove、Rosa M. Claramunt、M. Ángeles García、M. Dolores Santa Maria、Ibon Alkorta、José Elguero

  DOI：10.1016/j.tet.2007.06.007

  日期：2007.8

  The tautomerism in the solid state and in solution of five 4-bromo-1H-pyrazoles has been studied by multinuclear magnetic resonance spectroscopy and, for one of them, by X-ray crystallography (3,4-dibromo-5-phenyl-1H-pyrazole). When there is a bromine atom at position 3(5), in all cases, the tautomer present in the solid state is the 3-bromo one. In solution, the same tautomer is the major one. DFT calculations justify the predominance of 3-bromo tautomers over 5-bromo ones and provide some useful chemical shifts obtained through GIAO calculations. (c) 2007 Elsevier Ltd. All rights reserved.