4-(4-氨基苯氧基)苯甲腈 | 17076-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-氨基苯氧基)苯甲腈
• 中文别名: 4-(4-氨基苯氧基)苄腈
• 英文名称: 4-(4-aminophenoxy)benzonitrile
• CAS: 17076-69-6
• 化学式: C₁₃H₁₀N₂O
• mdl: MFCD00197201
• 分子量: 210.235
• InChiKey: YDNICCZCAISDAG-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  393.2±27.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：
  59
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(4-Aminophenoxy)benzonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-(4-Aminophenoxy)benzonitrile
CAS number: 17076-69-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H10N2O
Molecular weight: 210.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(4-氨基苯氧基)苯甲腈 在 盐酸 、 氢氧化钾 、 potassium carbonate 、 sodium nitrite 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 4-[4-[2-Oxo-3-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)propyl]sulfanylphenoxy]benzonitrile
  参考文献：
  名称：

  Phenoxyphenyl Sulfone N-Formylhydroxylamines (Retrohydroxamates) as Potent, Selective, Orally Bioavailable Matrix Metalloproteinase Inhibitors

  摘要：

  A novel series of sulfone N-formylhydroxylamines (retrohydroxamates) have been investigated as matrix metalloproteinases (MMP) inhibitors. The substitution of the ether linkage of ABT-770 (5) with a sulfone group 13a led to a substantial increase in activity against MMP-9 but was accompanied by a loss of selectivity for inhibition of MMP-2 and -9 over MMP-1 and diminished oral exposure. Replacement of the biphenyl P1' substituent with a phenoxyphenyl group provided compounds that are highly selective for inhibition of MMP-2 and -9 over MMP-1. Optimization of the substituent adjacent to the retrohydroxamate center in this series led to the clinical candidate ABT-518 (6), a highly potent, selective, orally bioavailable MMP inhibitor that has been shown to significantly inhibit tumor growth in animal cancer models.

  DOI：

  10.1021/jm0103920
• 作为产物：
  描述：

  4-羟基苯甲腈 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 4-(4-氨基苯氧基)苯甲腈
  参考文献：
  名称：

  氨基苯并噻唑作为N型和T型钙通道阻滞剂的合成与评价

  摘要：

  N型和T型钙离子通道均与疼痛传递有关，并且N型通道是治疗神经性疼痛的有效靶点。对一系列取代的氨基苯并噻唑的SAR研究在基于FLIPR的细胞内钙反应测定法中测定了在Ca V 2.2和Ca V 3.2通道的效价，确定了与阳性对照Z160具有可比活性的五种化合物的子集。这些化合物可能构成开发药物前导和工具化合物的基础，这些化合物和工具化合物用于评估Ca V 2.2和Ca V 3.2通道的可变调节的体内作用。

  DOI：

  10.1016/j.bmc.2018.03.031

文献信息

• Correlation between molecular dipole moment and centrosymmetry in some crystalline diphenyl ethers
  作者：Archan Dey、Gautam R. Desiraju

  DOI：10.1039/b502516h

  日期：——

  The presence of a large molecular dipole moment in diphenyl ethers leads unequivocally to a centrosymmetric crystal structure.

  二苯醚中大分子偶极矩的存在无疑导致了中心对称的晶体结构。
• TDP-43 Modulation by Tau-Tubulin Kinase 1 Inhibitors: A New Avenue for Future Amyotrophic Lateral Sclerosis Therapy
  作者：Vanesa Nozal、Loreto Martínez-González、Marta Gomez-Almeria、Claudia Gonzalo-Consuegra、Paula Santana、Apirat Chaikuad、Eva Pérez-Cuevas、Stefan Knapp、Daniel Lietha、David Ramírez、Sabrina Petralla、Barbara Monti、Carmen Gil、Angeles Martín-Requero、Valle Palomo、Eva de Lago、Ana Martinez

  DOI：10.1021/acs.jmedchem.1c01942

  日期：2022.1.27

  phosphorylates TDP-43 in cellular and animal models; thus, TTBK1 inhibitors emerge as a promising therapeutic strategy for ALS. The design, synthesis, biological evaluation, kinase–ligand complex structure determination, and molecular modeling studies confirmed novel pyrrolopyrimidine derivatives as valuable inhibitors for further development. Moreover, compound 29 revealed good brain penetration in vivo and was

  肌萎缩侧索硬化症（ALS）是一种致命的神经退行性疾病，没有任何有效的治疗方法。蛋白 TDP-43 是散发性和熟悉的患者 ALS 的病理标志。TDP-43 的翻译后修饰促进其在细胞质中的聚集。Tau-微管蛋白激酶 (TTBK1) 在细胞和动物模型中磷酸化 TDP-43；因此，TTBK1 抑制剂成为一种有前途的 ALS 治疗策略。设计、合成、生物学评价、激酶-配体复杂结构测定和分子建模研究证实了新型吡咯并嘧啶衍生物作为进一步开发的有价值的抑制剂。此外，化合物29在体内显示出良好的脑渗透性并且能够降低 TDP-43 磷酸化，不仅在细胞培养中，而且在转基因 TDP-43 小鼠的脊髓中。在体内也证实了向 M2 抗炎小胶质细胞的转变。这两项活动都导致了小鼠运动神经元的保存，建议吡咯并嘧啶29作为未来 ALS 治疗的有价值的先导化合物。
• Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species
  作者：Yanan Dong、Peiju Yang、Shizhen Zhao、Yuehui Li

  DOI：10.1038/s41467-020-17939-2

  日期：——

  pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic

  含氰化合物是重要的药物、农用化学品和有机材料。传统的氰化方法通常依赖于有毒金属氰化物的使用，这些氰化物具有严重的处置、储存和运输问题。因此，越来越需要开发通用且有效的催化方法来生产无氰腈。在这里，我们报告了使用 CO 2 /NH 3对有机氯化物进行还原氰化作为亲电子 CN 源。使用三齿膦配体 Triphos 可以使多种芳基和脂肪族氯化物在镍催化下氰化，从而以良好的收率和优异的官能团耐受性生产所需的腈产物。廉价且在工作台上稳定的尿素也被证明是合适的 CN 来源，表明具有广阔的应用潜力。机理研究表明，Triphos-Ni(I) 物种负责涉及异氰酸酯中间体的还原性 CC 偶联方法。该方法扩展了还原氰化在无氰条件下合成功能化腈化合物的应用潜力，这对于（同位素标记）药物的安全合成具有重要价值。
• [EN] SORAFENIB ANALOGS AND USES THEREOF<br/>[FR] ANALOGUES DE SORAFENIB ET LEURS UTILISATIONS
  申请人：UNIV COLUMBIA

  公开号：WO2015051149A1

  公开（公告）日：2015-04-09

  The present invention provides, inter alia, compounds according to formula I. Also provided are pharmaceutical compositions and kits containing such compounds. Methods for using such compounds, compositions, and kits for treating a subject having system xc-, dysregulation for activating ferroptosis, for inhibiting system xc- in a cell, and for monitoring treatment of a subject having system xc- dysregulation are provided as well.

  本发明提供了根据式I的化合物，还提供了含有这种化合物的药物组合物和试剂盒。还提供了使用这种化合物、组合物和试剂盒治疗具有系统xc-失调以激活铁死亡、在细胞中抑制系统xc-以及监测具有系统xc-失调的受试者治疗的方法。
• [EN] 3,4-DISUBSTITUTED MALEIMIDES FOR USE AS VASCULAR DAMAGING AGENTS<br/>[FR] MALEIMIDES 3,4-DISUBSTITUES UTILISES EN TANT QU'AGENTS DE DEGRADATION VASCULAIRE
  申请人：ASTRAZENECA AB

  公开号：WO2005102997A1

  公开（公告）日：2005-11-03

  This invention relates to novel compounds of Formula (I) for use as vascular damaging agents: Formula (I) wherein Rl, R7, R8, R9, ARI, AR2, AR3, p, q and r are as described in the specification. The invention also relates to methods for preparing compounds of Formula (I), to their use as medicaments (including methods for the treatment of angiogenesis or disease states associated with angiogenesis) and to pharmaceutical compositions containing compounds of Formula (I).

  本发明涉及用作血管损伤剂的新化合物的公式（I）：公式（I）其中Rl、R7、R8、R9、ARI、AR2、AR3、p、q和r如规范中所述。该发明还涉及制备公式（I）化合物的方法，它们作为药物的用途（包括用于治疗血管生成或与血管生成相关的疾病状态的方法）以及含有公式（I）化合物的药物组合物。