5-amino-3-methyl-4-(3-nitrophenylazo)-pyrazole | 947731-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-amino-3-methyl-4-(3-nitrophenylazo)-pyrazole
• 英文别名: 5-methyl-4-[(3-nitrophenyl)hydrazono]-4H-pyrazol-3-ylamine；5-methyl-4-[(3-nitrophenyl)diazenyl]-1H-pyrazol-3-amine
• CAS: 947731-75-1
• 化学式: C₁₀H₁₀N₆O₂
• 分子量: 246.228
• InChiKey: NFYORNMHVKCDFC-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C(Solvent: Ethanol)
• 沸点：
  549.3±50.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-amino-3-methyl-4-(3-nitrophenylazo)-pyrazole 在 盐酸 、 羟胺 、 溶剂黄146 、 sodium nitrite 作用下， 生成 4-(4'-(m-nitrophenylazo)-3'-methyl-1'H-pyrazol-5'-ylazo)-5-hydroxy-3-methylisoxazole
  参考文献：
  名称：

  含有吡唑和异恶唑的分散双偶氮染料的合成、表征和吸收性能研究

  摘要：

  摘要 本研究合成了在邻、间、对位被甲基、硝基和氯取代的新型杂环双偶氮分散染料(4a-4j)。这些新合成的十种双偶氮分散染料通过元素分析和光谱技术进行了表征。获得了溶解在六种溶剂中的新型合成染料的光谱数据。还报告了六种不同的酸性和碱性溶液的影响。此外，还详细探讨了这些十种新型杂环双偶氮分散染料在其邻、间和对位的吸收能力。

  DOI：

  10.1016/j.molstruc.2018.12.033
• 作为产物：
  描述：

  间硝基苯胺 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 5-amino-3-methyl-4-(3-nitrophenylazo)-pyrazole
  参考文献：
  名称：

  新型2,4-二羟基喹啉染料的抗癌，抗菌和DNA保护分析

  摘要：

  通过5-氨基-4-苯基偶氮-3-甲基-1H-吡唑衍生物与2,4-二羟基喹啉的反应合成了一系列新的2,4-二羟基喹啉衍生的二偶氮染料。通过各种分光光度法，例如FT-IR，1 H-NMR和元素分析来鉴定获得的染料的结构。还检查了合成的化合物的不同生物活性，包括DNA保护，抗微生物和抗癌活性。发现化合物3b对革兰氏阳性细菌最有效。对所有化合物都进行了DNA保护分析，发现化合物3h和3j具有与DNA结合的高能力。此外，化合物3h和3j对HeLa和PC3癌细胞系显示出细胞毒性。基于它们对细菌和癌细胞系的作用，这些化合物有可能被用作药物或药物添加剂。

  DOI：

  10.1016/j.dyepig.2018.04.040

文献信息

• Synthesis and Tautomeric Structure of 3,6-bis(arylazo)pyrazolo [1,5-<i>a</i>]pyrimidine-5,7(4<i>H</i>,6<i>H</i>)-diones
  作者：Ahmad S. Shawali、Mosselhi A. N. Mosselhi、Thoraya A. Farghaly、Mohamed R. Shehata、Nagla M. Tawfik

  DOI：10.3184/030823408x339782

  日期：2008.8

  Two series of 3,6-bis(arylazo)pyrazolo[1,5-a]pyrimidine-5,7-diones were prepared, and their acid dissociation constant pKas were determined and correlated with the Hammett equation. The results of these correlations, together with the spectroscopic data, indicated that the title compounds exist predominantly in the 3-arylazo-6-arylhydrazonopyrazolo[1,5-a]pyrimidine-5,7-dione tautomeric form, both in

  制备了两个系列的 3,6-双（芳基偶氮）吡唑并 [1,5-a] 嘧啶-5,7-二酮，测定了它们的酸解离常数 pKas，并与哈米特方程相关联。这些相关性的结果以及光谱数据表明，标题化合物主要以 3-芳基偶氮-6-芳基肼基吡唑并[1,5-a]嘧啶-5,7-二酮互变异构形式存在，无论是固体还是溶液相。
• Synthesis and absorption abilities of pyrazolo[5,1-c][1,2,4]triazine-based disperse dyes
  作者：F. Karcı、F. Karcı

  DOI：10.1007/s10593-013-1268-3

  日期：2013.6

  A series of 13 novel pyrazolo[5,1-c][1,2,4]triazine-based disperse dyes was synthesized by heating ethyl pyrazolylhydrazonocyanoacetate in glacial acetic acid. Solvent and acid-base influences on the wavelength of maximum absorption have been studied.

  通过在冰醋酸中加热吡唑基肼基氰基氰基乙酸乙酯，合成了13种新颖的吡唑并[5,1- c ] [1,2,4]三嗪基分散染料。研究了溶剂和酸碱对最大吸收波长的影响。
• New coumarin-based disperse disazo dyes: Synthesis, spectroscopic properties and theoretical calculations
  作者：Fati Yıldırım、Aykut Demirçalı、Fikret Karcı、Alpaslan Bayrakdar、Pınar Tunay Taşlı、H.Hüseyin Kart

  DOI：10.1016/j.molliq.2016.08.008

  日期：2016.11

  razoles (3a-l) have been diazotised and coupled with 4-hydroxycoumarin to give rise to the coumarin-based disperse disazo dyes (3a-l). The newly synthesized twelve coumarin-based disperse disazo dyes have been characterized by using the elemental analysis and the spectral methods. The solvatochromic behavior of these dyes in various solvents is evaluated. Substituent, acid and base effects on the visible

  已经将5-氨基-4-芳基偶氮-3-甲基-1H-吡唑（3a - 1）重氮化并与4-羟基香豆素偶联以产生基于香豆素的分散二偶氮染料（3a - 1）。通过元素分析和光谱方法对新合成的十二种香豆素基分散型二偶氮染料进行了表征。评估了这些染料在各种溶剂中的溶剂变色行为。取代基，酸和碱对在o-，m-和p处被吸电子和供电子基团取代的染料的可见吸收光谱的影响-位置也有详细报道。还使用基态下基于密度泛函理论（DFT）的从头算方法，对本文中考虑的化合物的分子几何结构和光谱性质进行了分析。从DFT获得的理论结果与实验结果相符。
• Disazo dyes containing pyrazole and indole moieties: Synthesis, characterization, absorption characteristics, theoretical calculations, structural and electronic properties
  作者：Çiğdem Karabacak Atay、Yeşim Kara、Merve Gökalp、Izzet Kara、Tahir Tilki、Fikret Karci

  DOI：10.1016/j.molliq.2016.01.031

  日期：2016.3

  recorded and chemical shifts of the molecules were compared to TMS by using the Gauge-Independent Atomic Orbital (GIAO) method. A study on the electronic and optical properties, absorption wavelengths, excitation energy and dipole moment is performed using DFT method. NBO analysis is carried out to picture the charge transfer between the localized bonds and lone pairs. All spectroscopic properties examined

  通过5-氨基-4-芳基偶氮-3-甲基-1H-吡唑2a-2m的重氮化并与2-甲基吲哚偶联制备了新合成的十三种分散二偶氮染料3a-3m。通过紫外可见光谱，傅立叶变换红外光谱，1 H NMR和元素分析对它们的结构进行了表征。研究了在不同溶剂中的溶剂变色性质。此外，还告知了酸和碱对染料可见吸收光谱的影响。此外，理论振动频率已经定标，并与相应的实验数据进行了比较。1个记录1 H NMR光谱，并使用不依赖于量规的原子轨道（GIAO）方法将分子的化学位移与TMS进行比较。使用DFT方法对电子和光学性质，吸收波长，激发能和偶极矩进行了研究。进行NBO分析以描绘局部键和孤对之间的电荷转移。计算结果支持了用实验技术检查的所有光谱特性。
• The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3-amino-5-hydroxy-1-phenylpyrazole
  作者：Fati Karcı、Aykut Demirçalı、Fikret Karcı、İzzet Kara、Fatih Ucun

  DOI：10.1016/j.molstruc.2009.06.040

  日期：2009.10

  In this study 5-amino-4-arylazo-3-methyl-1H-pyrazoles (1a-1m) were diazotised and coupled with 3amino-5-hydroxy-1-phenylpyrazole to give disperse disazo dyes (2a-2m). The newly synthesized 13 disperse disazo dyes were characterized by elemental analysis and spectral methods. The solvatochromic behaviour of these disperse disazo dyes in various solvents was evaluated. Substituent, acid and base effects on the visible absorption spectra of the disperse disazo dyes substituted with electron-withdrawing and electron-donating groups at their o-, m-, p-position were also reported in detail. Additionally, theoretical calculations are performed for the disazo dyes. The molecular geometry and chemical shift are calculated by using ab initio calculations based on the density functional theory (DFT) in the ground state. The results obtained are in agreement with the experimental results. (C) 2009 Elsevier B.V. All rights reserved.