1-(4-(N,N-dimethylamino)phenylazo)naphthalen-2-ol | 25023-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-(N,N-dimethylamino)phenylazo)naphthalen-2-ol
• 英文别名: 1-[4-(dimethylamino)-phenyldiazenyl]-2-naphthol；1-(4-Dimethylamino-phenylazo)-[2]naphthol；(N.N-Dimethyl-anilin)-(4 azo 4)-naphthol-(2)；1-{[4-(Dimethylamino)phenyl]diazenyl}-2-naphthol；1-[[4-(dimethylamino)phenyl]diazenyl]naphthalen-2-ol
• CAS: 25023-32-9
• 化学式: C₁₈H₁₇N₃O
• 分子量: 291.352
• InChiKey: KSGXGIDRHWKRFO-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182 °C
• 沸点：
  506.0±35.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-二甲基苯胺 在 盐酸 、 丙酮 、 sodium nitrite 作用下， 生成 1-(4-(N,N-dimethylamino)phenylazo)naphthalen-2-ol
  参考文献：
  名称：

  794.将重氮基团直接引入芳香核。第一部分：碱性反应，由聚烷基苯，苯酚醚，苯酚和芳族叔胺生成重氮盐

  摘要：

  DOI：

  10.1039/jr9570004003

文献信息

• Substituent Effect on the Tautomerization of 1-Arylazonaphthalen-2-ols by Mass Spectrometric Analysis
  作者：Shaw-Tao Lin、Lee-Hui Lin、Yi-Cang Lin、Mei-Fan Ding

  DOI：10.1002/jccs.201400305

  日期：2015.3

  An electron‐ionization (EI) mass spectra of a series of 1‐arylazonaphthalen‐2‐ols was obtained for studying the substituent effect on the fragmentation. The correlation between the ratio, molecular ion and fragment ion, and Hammett’s constants is applied to examine the effect of the substituent on the fragmentation. The negative correction between the ratio, Imolecular ion/(I171amu + I143amu + I115amu)

  获得了一系列1-芳基氮杂萘-2-醇的电子电离（EI）质谱图，以研究取代基对碎片的影响。比率，分子离子和碎片离子之间的相关性以及Hammett常数用于检查取代基对碎片的影响。I分子离子/（I 171amu + I 143amu + I 115amu）之比与Hammett常数之间的负校正表示吸电子基团使分子离子不稳定。异常的远距离氢转移显示了在裂解过程中的重要作用
• New Dry Arenediazonium Salts, Stabilized to an Exceptionally High Degree by the Anion of o-Benzenedisulfonimide
  作者：Margherita Barbero、Marco Crisma、Iacopo Degani、Rita Fochi、Paolo Perracino

  DOI：10.1055/s-1998-2132

  日期：1998.8
• Two azo pigments based on β-naphthol
  作者：Martin U. Schmidt、Jürgen Brüning、Daniela Wirth、Michael Bolte

  DOI：10.1107/s0108270108023421

  日期：2008.9.15

  There has been much discussion in the literature of the azo hydrazone tautomerism of pigments. All commercial azo pigments with beta-naphthol as the coupling compound adopt the hydrazone tautomeric form (Ph - NH - N = C) in the solid state. In contrast, the red pigments 1-[4-(dimethylamino)-phenyldiazenyl]-2-naphthol, C(18)H(17)N(3)O, (1a), and 1-[4(diethylamino)phenyldiazenyl]-2-naphthol, C(20)H(21)N(3)O, (1b), have been reported to be azo tautomers or a mixture of azo and hydrazone tautomers in the solid state. To prove these observations, both compounds were synthesized, recrystallized and their crystal structures redetermined by single-crystal structure analysis. Difference electron-density maps show that the H atoms of the hydroxyl groups are indeed bonded to the O atoms. Nevertheless, a small amount of the hydrazone form seems to be present. Hence, the compounds are close to being 'real' azo compounds. Compound (1a) crystallizes with a herring-bone structure and compound (1b) forms a rare double herring-bone structure.
• DE87585
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