5-(phenylazo)salicylic acid | 3147-53-3

• 物质功能分类: 化学试剂 - 有机试剂 - 叠氮
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 5-(phenylazo)salicylic acid
• 英文别名: 5‐[(E)‐2‐phenyl‐1‐diazenyl]‐2‐hydroxybenzoic acid；5-[(E)-2-(phenyl)-1-diazenyl]-2-hydroxybenzoic acid；5-[(E)-2-phenyl-1-diazenyl]-2-hydroxybenzoic acid；(E)-2-hydroxy-5-(phenyldiazenyl)benzoic acid；2-hydroxy-5E-(phenyldiazenyl)benzoic acid；2-hydroxy-5-(phenyldiazenyl)benzoic acid；5-(phenyldiazenyl)salicylic acid
• CAS: 3147-53-3
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: JHDYSXXPQIFFJZ-CCEZHUSRSA-N

物化性质

• 熔点：
  220.5 °C
• 沸点：
  472.7±40.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  丙酮（少量溶解）、水基（少量溶解）、甲醇（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.25
• 氢给体数：
  2.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2927000090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，干燥且密封。

反应信息

• 作为反应物：
  描述：

  5-(phenylazo)salicylic acid 生成 5-氨基水杨酸
  参考文献：
  名称：

  SCHAFER, WINFRIED;HAWA, SILKE

  摘要：

  DOI：
• 作为产物：
  描述：

  苯胺 、 水杨酸 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 以33%的产率得到5-(phenylazo)salicylic acid
  参考文献：
  名称：

  5-[（E）-2-（芳基）-1-二氮烯基] -2-羟基苯甲酸的三有机锡（IV）配合物的合成与表征.. ：三苯基锡5-[（E）- 2-（芳基）-1-二氮烯基] -2-羟基苯甲酸酯（芳基=苯基，2-甲基苯基，3-甲基苯基和4-甲氧基苯基）

  摘要：

  的三苯基锡和三Ñ一些5 -butyltin络合物- [（ë）-2-（芳基）-1-二氮烯基] -2-羟基苯甲酸已经合成和表征通过1 H-，13 C-，119 Sn的NMR，IR和119m SnMössbauer光谱技术与元素分析相结合。报道了三苯基锡5-[（E）-2-（芳基）-1-二氮烯基] -2-羟基苯甲酸酯的晶体结构（芳基=苯基，2-甲基苯基，3-甲基苯基和4-甲氧基苯基）。X射线和119 SnMössbauer数据均表明三苯锡配合物采用单体扭曲的四面体构型，且羧酸盐配体以单齿模式配位。相比之下，119 SnMössbauer光谱表明，每个三丁基锡配合物都是聚合的，具有跨三角形的双锥体几何结构，具有平面的SnBu 3单元和两个双齿形的羧酸根配位体衍生而来的顶端的羧基氧原子。这是一种固态的效果，既是119 Sn-NMR的和1 Ĵ（13 C- 117分之119 Sn）的耦合常数的数据表明在溶液中四面体几何形状的三苯基-和三-

  DOI：

  10.1016/s0022-328x(01)01024-5

文献信息

• Mono- and di-anionic coordination modes of arylazosalicylates in their bis(η5-cyclopentadienyl)titanium(IV) complexes: Syntheses and crystal structures
  作者：Tushar S. Basu Baul、Rajesh Manne、Edward R.T. Tiekink

  DOI：10.1016/j.ica.2018.09.076

  日期：2019.1

  techniques. The crystal and molecular structures of 3–9 have been determined by single crystal X-ray crystallography. Compounds 3 and 4 conform to the formula Cp2Ti(HLXASA-κO)2 with a monodentate carboxylate ligand while those of 5–9 conform to Cp2Ti(LXASA-κ2O1,O2) with the dianions chelating the titanium atoms via carboxylate-O and hydroxy-O atoms. The common feature of the molecular structures is the adoption

  摘要5-[（E）-2-（芳基）-1-二氮烯基] -2-羟基苯甲酸（H2LXASA）的双（η5-环戊二烯基）钛（IV）配合物，其中的芳基为X取代的苯环这样就合成了X = CH，COEt，CMe，CF，CCl，CBr和N。两种类型的钛（IV）化合物。（i）[Ti（η5-C5H5）2（O2CC6H3（OH-2）（N NC6H4（H-4）-5））2]（3）和[Ti（η5-C5H5）2（O2CC6H3（OH-2） ）（N NC6H4（OC2H5-4）-5））2]（4）和（ii）[Ti（η5-C5H5）2（O2CC6H3（O-2）（N NC6H4（CH3-4）-5））） ]（5），[Ti（η5-C5H5）2（O2CC6H3（O-2）（N NC6H4（F-4）-5））]（6），[Ti（η5-C5H5）2（O2CC6H3（O- 2）（N NC6H4（Cl-4）-5））]（7），[Ti（η5-C5H5）2（O2CC6H3（O-2）（N
• Benzoxazole derivatives for the prophylaxis and treatment of inflammatory bowel diseases
  申请人：Hikma Pharmaceuticals Co. Ltd.

  公开号：EP1688413A1

  公开（公告）日：2006-08-09

  The present invention relates to novel compounds for the prophylaxis and treatment of inflammatory bowel disease (IBD) via the administration of an effective amount in a suitable pharmaceutical dosage of agents that are active by themselves or can deliver tin the large intestine active forms of the drugs such as 5ASA or benzoxazole acetic acid or platelet activating factors. The mechanism of the release is based on bacterial cleavage of an azo linkage in the mammalian lower bowel to release the active compound(s).

  本发明涉及通过给予有效剂量的新化合物进行预防和治疗炎症性肠病（IBD），这些化合物以适当的药物剂量给药，这些化合物本身具有活性或者可以在大肠中释放药物的活性形式，如5-氨基水杨酸（5ASA）或苯并噁唑乙酸或血小板活化因子。释放机制基于细菌在哺乳动物下肠中裂解偶氮键来释放活性化合物。
• Novel compounds for the prophylaxis and treatment of inflammatory bowel diseases
  申请人：Jilani Jamal

  公开号：US20070043003A1

  公开（公告）日：2007-02-22

  Novel compounds are disclosed for the prophylaxis and treatment of inflammatory bowel disease (IBD) via the administration of an effective amount in a suitable pharmaceutical dosage of agents that are active by themselves or can deliver tin the large intestine active forms of the drugs such as 5ASA or benzoxazole acetic acid or platelet activating factors. The mechanism of the release is based on bacterial cleavage of an azo linkage in the mammalian lower bowel to release the active compound(s).

  揭示了用于预防和治疗炎症性肠病（IBD）的新化合物，通过在适当的药物剂量中给予能够自身活跃或能够在大肠中释放药物的活性形式的药剂，如5-氨基水杨酸（5ASA）或苯并噁唑乙酸或血小板活化因子。释放机制基于细菌在哺乳动物下肠中裂解偶氮键以释放活性化合物。
• <i>syn</i> and <i>anti</i> conformations in 2-hydroxy-5-[(<i>E</i>)-(4-nitrophenyl)diazenyl]benzoic acid and two related salts
  作者：Alexandr V. Yatsenko、Ksenia A. Paseshnichenko

  DOI：10.1107/s2053229614007827

  日期：2014.5.1

  The crystal structures of 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoic acid, C₁₃H₉N₃O₅, (I), ammonium 2-hydroxy-5-[(E)-phenyldiazenyl]benzoate, NH₄ ⁺·C₁₃H₉N₂O₃ ⁻, (II), and sodium 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoate trihydrate, Na⁺·C₁₃H₈N₃O₅ ⁻·3H₂O, (III), have been determined using single-crystal X-ray diffraction. In (I) and (III), the phenyldiazenyl and carboxylic acid/carboxylate groups are in an anti orientation with respect to each other, which is in accord with the results of density functional theory (DFT) calculations, whereas in (II), the anion adopts a syn conformation. In (I), molecules form slanted stacks along the [100] direction. In (II), anions form bilayers parallel to (010), the inner part of the bilayers being formed by the benzene rings, with the –OH and –COO⁻ substituents on the bilayer surface. The NH₄ ⁺ cations in (II) are located between the bilayers and are engaged in numerous N—H...O hydrogen bonds. In (III), anions form layers parallel to (001). Both Na⁺ cations have a distorted octahedral environment, with four octahedra edge-shared by bridging water O atoms, forming [Na₄(H₂O)₁₂]⁴⁺ units.

  2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoic acid, C13H9N3O5, (I)、2-hydroxy-5-[(E)-phenyldiazenyl]benzoate ammonium, NH4 +-C13H9N2O3 -，(II) 和三水 2-羟基-5-[(E)-(4-硝基苯基)偶氮]苯甲酸钠，Na+-C13H8N3O5 -3H2O，(III) 的单晶 X 射线衍射测定。在(I)和(III)中，苯基二氮基和羧酸基/羧酸基彼此呈反方向，这与密度泛函理论（DFT）计算的结果一致，而在(II)中，阴离子采用了合成构象。在(I)中，分子沿[100]方向形成斜堆。在(II)中，阴离子形成平行于(010)方向的双分子层，双分子层的内部由苯环形成，-OH 和 -COO- 取代基位于双分子层表面。(II) 中的 NH4 +阳离子位于双分子层之间，并与许多 N-H...O 氢键结合。在(III)中，阴离子形成与(001)平行的层。两个 Na+阳离子都具有畸变的八面体环境，四个八面体的边缘都有桥接的水 O 原子，形成[Na4(H2O)12]4+单元。
• Crystal and Molecular Structures of Four Salts from Isopropylamine, Cinnamic Acid, 2-Hydroxy-5-(phenyldiazenyl)benzoic Acid, m-Phthalic Acid and 2,6-Pyridinedicarboxylic Acid
  作者：Shouwen Jin、Chao Feng、Xianhong Wen、Li Jin、Daqi Wang

  DOI：10.1007/s10870-016-0634-2

  日期：2016.3

  Four isopropylamine derived supramolecular salts were synthesized and characterized by X-ray crystallography, IR, mp, and elemental analysis. Compound 1 crystallizes in the monoclinic, space group P2(1), with a = 7.1957(6) Å, b = 6.4365(5) Å, c = 13.3816(11) Å, α = 90°, β = 92.7390(10)°, γ = 90°, V = 619.06(9) Å3, Z = 2. Compound 2 crystallizes in the monoclinic, space group P2(1)/n, with a = 9.2739(8) Å, b = 4.8837(3) Å, c = 35.222(3) Å, α = 90°, β = 92.9800(10)°, γ = 90°, V = 1593.1(2) Å3, Z = 4. Compound 3 crystallizes in the orthorhombic, space group Pnma, with a = 13.1220(11) Å, b = 19.9560(16) Å, c = 6.3290(5) Å, α = 90°, β = 90°, γ = 90°, V = 1657.3(2) Å3, Z = 4. Compound 4 crystallizes in the monoclinic, space group P2(1)/c, with a = 7.0436(5) Å, b = 17.2844(13) Å, c = 13.0970(11) Å, α = 90°, β = 97.2680(10)°, γ = 90°, V = 1581.7(2) Å3, Z = 4. All supramolecular salts bear intermolecular N–H···O hydrogen bonds. Further analysis of the crystal packing of 1–4 suggests that the CH3–O and CH3–Cπ interactions also have equal importance in the structure extension as the classical hydrogen bonds. In conclusion, the discrete ions can be architectured into 1D–3D structures by the collective non-covalent interactions. The crystal structures of the salts from isopropylamine, cinnamic acid, 2-hydroxy-5-(phenyldiazenyl)benzoic acid, m-phthalic acid, and 2,6-pyridinedicarboxylic acid are predominantly stabilized by the classical hydrogen bonds as well as CH3–O, and CH3–Cπ interactions, leading to 1D–3D structures.

  合成了四种异丙胺衍生的超分子盐，并通过 X 射线晶体学、红外、熔点和元素分析进行​​了表征。化合物 1 结晶为单斜晶系空间群 P2(1)，a = 7.1957(6) Å，b = 6.4365(5) Å，c = 13.3816(11) Å，α = 90°，β = 92.7390(10) °，γ = 90°，V = 619.06(9) Å3，Z = 2。化合物 2 结晶为单斜晶系，空间群 P2(1)/n，a = 9.2739(8) Å，b = 4.8837(3) Å, c = 35.222(3) Å, α = 90°, β = 92.9800(10)°, γ = 90°, V = 1593.1(2) Å3, Z = 4。化合物 3 以斜方空间群 Pnma 结晶，其中 a = 13.1220(11) Å、b = 19.9560(16) Å、c = 6.3290(5) Å、α = 90°、β = 90°、γ = 90°、V = 1657.3(2) Å3、Z = 4. 化合物 4 结晶为单斜晶系，空间群 P2(1)/c，a = 7.0436(5) Å, b = 17.2844(13) Å, c = 13.0970(11) Å, α = 90°, β = 97.2680(10)°, γ = 90°, V = 1581.7(2) Å3, Z = 4。所有超分子盐都带有分子间 N–H···O 氢键。对 1-4 晶体堆积的进一步分析表明，CH3-O 和 CH3-Cπ 相互作用在结构延伸中与经典氢键同样重要。总之，离散离子可以通过集体非共价相互作用构建成 1D-3D 结构。异丙胺、肉桂酸、2-羟基-5-(苯基二氮烯基)苯甲酸、间苯二甲酸和 2,6-吡啶二甲酸的盐的晶体结构主要通过经典氢键以及 CH3-O 来稳定，以及 CH3–Cπ 相互作用，形成 1D–3D 结构。