1-(4-diethylaminophenylazo)-2-hydroxynaphthalene | 4536-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-diethylaminophenylazo)-2-hydroxynaphthalene
• 英文别名: 1-[4-(diethylamino)-phenyldiazenyl]-2-naphthol；1-(p-diethylaminophenylazo)-2-naphthol；1-(4-diethylamino-phenylazo)-[2]naphthol；1-(4-Diaethylamino-phenylazo)-[2]naphthol；1-(4-Diethylamino-benzolazo)-naphthol-(2)；2-Naphthalenol, 1-[[4-(diethylamino)phenyl]azo]-；1-[[4-(diethylamino)phenyl]diazenyl]naphthalen-2-ol
• CAS: 4536-70-3
• 化学式: C₂₀H₂₁N₃O
• 分子量: 319.406
• InChiKey: PIJBAGBDXWEEAX-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  523.3±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper diacetate 、 1-(4-diethylaminophenylazo)-2-hydroxynaphthalene 在 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Gromov, D. N.; Zaitsev, B. E.; Traven', V. F., Russian Journal of Inorganic Chemistry, 1987, vol. 32, p. 389 - 392

  摘要：

  DOI：
• 作为产物：
  描述：

  2-萘酚 、 N,N-二乙基对苯二胺 在 sodium nitrite 作用下， 以 盐酸 、 水 为溶剂， 生成 1-(4-diethylaminophenylazo)-2-hydroxynaphthalene
  参考文献：
  名称：

  Two azo pigments based on β-naphthol

  摘要：

  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.

  DOI：

  10.1107/s0108270108023421

文献信息

• Traven', V. F.; Kostyuchenko, E. E.; Mkhitarov, R. A., Journal of Organic Chemistry USSR (English Translation), 1980, p. 922 - 930
  作者：Traven', V. F.、Kostyuchenko, E. E.、Mkhitarov, R. A.、Men'shikova, N. F.、Oreshin, M. M.、Stepanov, B. I.

  DOI：——

  日期：——
• Haessner, Rainer; Epperlein, Joachim; Marx, Joerg, Zeitschrift fur Chemie, 1980, vol. 20, # 12, p. 439 - 440
  作者：Haessner, Rainer、Epperlein, Joachim、Marx, Joerg

  DOI：——

  日期：——
• 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.
• Gromov, D. N.; Zaitsev, B. E.; Traven', V. F., Russian Journal of Inorganic Chemistry, 1987, vol. 32, p. 389 - 392
  作者：Gromov, D. N.、Zaitsev, B. E.、Traven', V. F.、Odinets, Z. K.

  DOI：——

  日期：——