4-chloro-1-(4-chlorophenyl)-1H-imidazole-5-carbaldehyde | 1181508-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-chloro-1-(4-chlorophenyl)-1H-imidazole-5-carbaldehyde
• 英文别名: 5-chloro-3-(4-chlorophenyl)imidazole-4-carbaldehyde
• CAS: 1181508-03-1
• 化学式: C₁₀H₆Cl₂N₂O
• 分子量: 241.076
• InChiKey: QTTPQRUMGPORKP-UHFFFAOYSA-N

物化性质

• 熔点：
  159-160 °C(Solvent: Ethanol)
• 沸点：
  402.8±35.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-1-(4-chlorophenyl)-1H-imidazole-5-carbaldehyde 在 potassium permanganate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.5h， 以82%的产率得到4-chloro-1-(4-chlorophenyl)-1H-imidazole-5-carboxylic acid
  参考文献：
  名称：

  Polyfunctional imidazoles: V. Synthesis of 1-aryl-4-chloro- 5-di(tri)fluoromethyl-1H-imidazoles

  摘要：

  1-Aryl-4-chloro-1H-imidazole-5-carbaldehydes and 1-aryl-4-chloro-1H-imidazole-5-carboxylic acids reacted with sulfur(IV) fluoride to give, respectively, 1-aryl-4-chloro-5-difluoromethyl- and 1-aryl-4-chloro-5-trifluoromethyl-1H-imidazoles.

  DOI：

  10.1134/s1070428012030104
• 作为产物：
  描述：

  N-(4-chloro-phenyl)-glycine amide 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 水 作用下， 以49%的产率得到4-chloro-1-(4-chlorophenyl)-1H-imidazole-5-carbaldehyde
  参考文献：
  名称：

  Polyfunctional imidazoles: I. Synthesis of 1-substituted 4-chloro-1H-imidazole-5-carbaldehydes by Vilsmeier-Haack reaction

  摘要：

  2-[Alkyl(aryl)amino]acetamides in reaction with Vilsmeier-Haack reagent afforded 1-alkyl(aryl)-4-chloro-1H-imidazole-5-carbaldehydes.

  DOI：

  10.1134/s1070428009080168

文献信息

• Polyfunctional imidazoles: XIV. 4-sulfonyl-5-formyl-1H-imidazoles
  作者：A. N. Grozav、V. A. Chornous、V. I. Dorokhov、M. V. Vovk

  DOI：10.1134/s1070428017100104

  日期：2017.10

  5-formylimidazole-4-sulfonamides and aryl sulfonates. The reaction of 1-aryl-5-formyl-1H-imidazole-4-sulfonyl chlorides with sodium azide, followed by reduction of the resulting sulfonyl azides, led to the formation of N-unsubstituted 5-formylimidazole-4-sulfonamides, and the reaction with alcohols, to 5-formylimidazole-4-sulfonic acids.

  1-芳基-4-苄基硫烷基-1 H-咪唑-5-甲醛的氧化氯化反应生成1-芳基-5-甲酰基-1 H-咪唑-4-磺酰基氯，与仲胺和酚反应生成相应的N，N-二取代的5-甲酰咪唑-4-磺酰胺和芳基磺酸酯。1-芳基-5-甲酰基-1 H-咪唑-4-磺酰氯与叠氮化钠的反应，然后还原生成的磺酰基叠氮化物，导致形成N-未取代的5-甲酰咪唑-4-磺酰胺，以及与醇反应，生成5-甲酰咪唑-4-磺酸。
• Polyfunctional imidazoles: X. Synthesis of 4-chloro-5-(2-nitroalkenyl)-1H-imidazoles and their reaction with 5-methyl-2,4-dihydro-3H-pyrazol-3-one
  作者：V. A. Chornous、A. N. Grozav、O. Ya. Mel’nik、V. V. Pirozhenko、M. V. Vovk

  DOI：10.1134/s1070428015040132

  日期：2015.4

  Condensation of 1-aryl-4-chloro-1H-imidazole-5-carbaldehydes with nitroalkanes in the presence of anhydrous ammonium acetate gave 4-chloro-5-(2-nitroalkenyl)-1H-imidazoles which reacted with 5-methyl-2,4-dihydro-3H-pyrazol-3-one according to the Michael addition scheme with formation of 4-[1-(4-chloro-1H-imidazol-5-yl)-2-nitroalkyl]-5-methyl-1H-pyrazol-3-ols.
• Polyfunctional imidazoles: III. Synthesis of 1-aryl-2,4-dihalo-1H-imidazole-5-carboxylic acids and their derivatives
  作者：V. A. Chornous、A. N. Grozav、M. V. Vovk

  DOI：10.1134/s1070428011080124

  日期：2011.8

  1-Aryl-4-chloro(2,4-dichloro)-1H-imidazole-5-carbaldehydes reacted with N-bromosuccinimide affording bromides of 1-aryl-2-bromo(2,4-dichloro)-1H-imidazole-5-carboxylic acids which were converted into the corresponding acids, esters, and amides.
• Polyfunctional imidazoles: VII. 1-aryl-4-chloro-5-[hydroxy(halo)methyl]-1H-imidazoles and their derivatives
  作者：V. A. Chornous、A. N. Grozav、D. V. Klyukovskii、A. V. Bezdudnyi、M. V. Vovk

  DOI：10.1134/s1070428013040131

  日期：2013.4

  The reduction of 1-aryl-4-chloro-1H-imidazole-5-carbaldehydes with sodium tetrahydridoborate gave 1-aryl-4-chloro-1H-imidazol-5-ylmethanols which were converted into 5-chloromethyl and 5-fluoromethyl derivatives. 1-Aryl-4-chloro-5-chloromethyl-1H-imidazoles reacted with sodium azide, secondary amines, thiols, and triphenylphosphine to produce the corresponding products of chlorine replacement in the 5-chloromethyl group.
• Polyfunctional imidazoles: IX. Synthesis of 1-aryl-5-(2-aryl-3,4-dihydro-2H-pyrrol-4-yl)-4-chloro-1H-imidazoles
  作者：O. Ya. Mel’nik、V. A. Chornous、M. V. Vovk

  DOI：10.1134/s1070428015020189

  日期：2015.2

  1-Aryl-3-(1-aryl-4-chloro-1H-imidazol-5-yl)prop-2-en-1-ones prepared from 1-aryl-4-chloro-1H-imidazole-5-carbaldehydes and methyl aryl ketones reacted with nitromethane affording 1-aryl-3-(1-aryl-4-chloro-1H-imidazol-5-yl)-4-nitrobutan-1-ones which were reduced with zink in acetic acid to obtain 1-aryl-5-(2-aryl-3,4-dihydro-2H-pyrrol-4-yl)-4-chloro-1H-imidazoles.