4-(4-硝基苯偶氮)苯磷二酚 | 843-33-4

• 物质功能分类: 有机原料 - 重氮、偶氮或氧化偶氮化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 中文名称: 4-(4-硝基苯偶氮)苯磷二酚
• 中文别名: 4-(4-硝基苯偶氮)邻苯二酚；4-(4-硝基苯偶氮)儿茶酚；4-(4-硝基苯偶氮基)-1,2-苯二酚；4-(4-硝基苯偶氮基)苯邻二酚；4-[(4-硝基苯基)偶氮]邻苯二酚
• 英文名称: 4-[(4-nitrophenyl)diazenyl]-1,2-benzenediol
• 英文别名: 4-[(4-nitrophenyl)azo]-1,2-benzenediol；4-(4-nitrophenylazo)catechol；4-(4-nitro-phenylazo)-pyrocatechol；4-(4-Nitro-phenylazo)-brenzcatechin；(4-Nitro-benzol)-(1 azo 4)-brenzcatechin；4'-Nitro-3.4-dioxy-azobenzol；4-[(4-nitrophenyl)diazenyl]benzene-1,2-diol
• CAS: 843-33-4
• 化学式: C₁₂H₉N₃O₄
• mdl: MFCD00014711
• 分子量: 259.221
• InChiKey: DGOZWUSVOBKXNR-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190°C
• 稳定性/保质期：
  在常温常压下稳定，应避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 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：
  111
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2927000090
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

4-(4-硝基苯偶氮)苯磷二酚MSDS英文版

反应信息

• 作为反应物：
  描述：

  2-氯乙基乙烯基醚 、 4-(4-硝基苯偶氮)苯磷二酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以75%的产率得到1-(3,4-bis(2-(vinyloxy)ethoxy)phenyl)-2-(4-nitrophenyl)diazene
  参考文献：
  名称：

  Synthesis and Properties of Novel Polyurethane Containing Nitrophenylazocatecholic Group as NLO Chromophore

  摘要：

  DOI：

  10.5012/bkcs.2012.33.2.695
• 作为产物：
  描述：

  邻苯二酚 、 4-硝基苯胺 在 盐酸 、 1-methyl-3-(3-trimethoxysilylpropyl)imidazolium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.08h， 以88%的产率得到4-(4-硝基苯偶氮)苯磷二酚
  参考文献：
  名称：

  亚硝酸离子液体1-（3-三甲氧基甲硅烷基丙基）-3-甲基咪唑鎓作为新型试剂，用于苯胺衍生物的高效重氮化和偶氮染料的原位合成

  摘要：

  合成了一种新型的离子液体1-（3-三甲氧基甲硅烷基丙基）-3-甲基咪唑鎓亚硝酸盐。这种离子液体被用作芳胺的重氮化了方便亚硝源为它们相应的重氮盐，其被转换成其相关的偶氮染料通过在原位与苯胺衍生物或酚类化合物偶氮耦合。苯胺在该离子液体中的重氮化反应和随后的偶氮偶合反应，可通过简单的实验程序，在较短的反应时间内，在0–5°C的条件下，以优异的产率产生相关的偶氮染料。

  DOI：

  10.1007/bf03249083

文献信息

• A new nitrite ionic liquid (IL-ONO) as a nitrosonium source for the efficient diazotization of aniline derivatives and in-situ synthesis of azo dyes
  作者：Hassan Valizadeh、Ashkan Shomali

  DOI：10.1016/j.dyepig.2010.11.010

  日期：2012.3

  affect the efficient diazotization of arylamines. The diazonium salts thus obtained were coupled, using standard experimental procedures, to a range of tertiary anilines, phenols and naphthols to afford the requisite azo dyes in good yield. The diazotization and subsequent azo-coupling generated the related azo dyes at 0–5 °C in short reaction times with a simple experimental procedure.

  合成了一种新的含特定任务的亚硝酸盐离子液体，该液体由N-甲基-N-羟丁基咪唑啉鎓氯化物的O-亚硝化反应衍生而来，并用作亚硝鎓离子的来源，以影响芳基胺的有效重氮化。使用标准的实验方法，将如此获得的重氮盐与一系列叔苯胺，苯酚和萘酚偶联，以高收率提供所需的偶氮染料。通过简单的实验程序，重氮化和随后的偶氮偶联在较短的反应时间内于0-5°C生成了相关的偶氮染料。
• Carboxyl and nitrite functionalized graphene quantum dots as a highly active reagent and catalyst for rapid diazotization reaction and synthesis of azo-dyes under solvent-free conditions
  作者：Hassan Valizadeh、Ashkan Shomali、Saideh Nourshargh、Rahim Mohammad-Rezaei

  DOI：10.1016/j.dyepig.2014.09.023

  日期：2015.2

  Carboxyl and nitrite functionalized graphene quantum dots was prepared from carboxyl and hydroxyl functionalized graphene quantum dots using NaNO2 in the absence of mineral acids. This functional group conversion was confirmed by FT-IR spectroscopy, photoluminescence and X-ray diffraction. The carboxyl and nitrite functionalized graphene quantum dots was used as an effective nitrosonium ion source and reusable catalyst for the efficient diazotization of a variety of arylamines without using any additional acid. Subsequent azo-coupling of these freshly prepared diazonium salts with a range of active aromatic compounds led to the requisite azo-dyes in excellent yields in very short reaction times with a simple experimental procedure. (C) 2014 Elsevier Ltd. All rights reserved.
• Witt; Mayer,F., Chemische Berichte, 1893, vol. 26, p. 1076
  作者：Witt、Mayer,F.

  DOI：——

  日期：——
• Laws of complex formation in a series of azo-substituted pyrocatechol derivatives and their tin(II) complexes
  作者：N. N. Basargin、E. R. Oskotskaya、I. N. Senchakova、Yu. G. Rozovskii

  DOI：10.1134/s0036023609100180

  日期：2009.10

  Physicochemical properties of new reagents, azo-substituted pyrocatechol derivatives and their tin(II) complexes, are studied. The acid-base properties of the hydroxy groups (pK'(i), pKaEuro(i)(3)), parameters of complex formation reactions (pH, temperature, time), and instability constants of the complexes formed (pK (i)) are determined. Quantitative correlations between the dissociation constants (pK'(a)) of the functional analytical group, and the electronic Hammett constant sigma for a substituent (pK'(a)-pH(50) of the complex formation reaction), as well as between pK'(a) and instability constants of the complexes (pK (a)), are established. The quantitative correlations established allow the prediction of the physicochemical properties of the reagents and tin(II) complexes with new reagents of this class with the same functional analytical group (FAG) but other substituents.
• Synthesis and Properties of Novel Nonlinear Optical Polyurethane Containing Nitrophenylazocatecholic Group
  作者：Mi Young Song、Mi Sung Kim、Byeongman Jeon、Ju-Yeon Lee

  DOI：10.1080/15421406.2012.710192

  日期：2012.12.3

  A novel Y-type polyurethane 3 containing 4-(4-nitrophenylazo)catecholic groups as nonlinear optical (NLO) chromophores was prepared and characterized. Polyurethane 3 is soluble in common organic solvents such as acetone and DMF. Polymer 3 shows a thermal stability up to 270 degrees C from TGA thermogram and the T-g value obtained from DSC thermogram is around 96 degrees C. The second harmonic generation (SHG) coefficient (d(33)) of poled polymer film at 1064 nm fundamental wavelength is 4.58 x 10(-9) esu. The dipole alignment exhibits a thermal stability even at 4 degrees C higher than T-g, and there is no SHG decay below 100 degrees C due to the partial main-chain character of the polymer structure, which is acceptable for nonlinear optical device applications.