4-(5-硝基苯并咪唑-2-基)苯胺 | 71002-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 4-(5-硝基苯并咪唑-2-基)苯胺
• 英文名称: 4-(5-nitro-1H-benzo[d]imidazol-2-yl)aniline
• 英文别名: 4-(6-nitro-1H-benzimidazol-2-yl)aniline
• CAS: 71002-88-5
• 化学式: C₁₃H₁₀N₄O₂
• 分子量: 254.248
• InChiKey: VQAXRPAGHNBDHU-UHFFFAOYSA-N

物化性质

• 熔点：
  283-285 °C(Solv: tetrahydrofuran (109-99-9))
• 沸点：
  551.3±56.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 储存条件：
  | 室温 干燥 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(5-Nitrobenzimidazol-2-yl)aniline
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-(5-Nitrobenzimidazol-2-yl)aniline
CAS number: 71002-88-5

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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: C13H10N4O2
Molecular weight: 254.2

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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-(5-硝基苯并咪唑-2-基)苯胺 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 生成 N-[4-(6-amino-1H-benzimidazol-2-yl)phenyl]-2,3-dichlorobenzamide
  参考文献：
  名称：

  取代的2-苯基-苯并咪唑衍生物：抑制过敏关键标志物的新型化合物。

  摘要：

  传统上，过敏和哮喘的药物治疗重点放在过敏级联反应的效应分子上，而忽略了在其发展中起早期作用的靶标。由于IgE对特应性疾病的扩展至关重要，因此我们确定并扩展了IgE反应的2-（取代苯基）-苯并咪唑抑制剂的新家族。药理活性取决于完整的苯基苯并咪唑-双酰胺主链，并通过存在由双环烷基或脂族和卤素取代的芳族基团组成的亲脂性端基来优化药理活性。这些化合物还抑制T细胞中的IL-4和IL-5应答以及B细胞上的CD23表达，其效力与其抑制IgE相似。

  DOI：

  10.1016/j.ejmech.2006.03.014
• 作为产物：
  描述：

  N-BOC-4-氨基苯甲酸 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4-(5-硝基苯并咪唑-2-基)苯胺
  参考文献：
  名称：

  Synthesis and evaluation of novel bacterial rRNA-binding benzimidazoles by mass spectrometry

  摘要：

  A series of novel benzimidazoles were efficiently synthesized using both solution- and solid-phase chemistry. These compounds were found to bind to the bacterial 16S ribosomal RNA A-site with micromolar affinities using unique mass spectrometry-based assays. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.031

文献信息

• [EN] INHIBITORS OF HEPATITIS C VIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：MERCK SHARP & DOHME

  公开号：WO2010111483A1

  公开（公告）日：2010-09-30

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种公式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20190127365A1

  公开（公告）日：2019-05-02

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种具有式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• [EN] BENZIMIDAZOLE DERIVATIVES FOR DNA METHYLATION INHIBITORS<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE POUR DES INHIBITEURS DE MÉTHYLATION DE L'ADN
  申请人：KAINOS MEDICINE INC

  公开号：WO2017039318A1

  公开（公告）日：2017-03-09

  The invention provides for DNA methylation inhibitors, and also methods and use of the compounds of the invention, by themselves or in combination with other therapies, for treating a disease in which DNA hypermethylation is found.

  这项发明提供了DNA甲基化抑制剂，以及该发明的化合物的方法和用途，可以单独使用或与其他疗法结合，用于治疗DNA高甲基化的疾病。
• Tuning Second-Order Optical Nonlinearities in Push-Pull Benzimidazoles
  作者：Antonio Carella、Roberto Centore、Alain Fort、Andrea Peluso、Augusto Sirigu、Angela Tuzi

  DOI：10.1002/ejoc.200300786

  日期：2004.6

  characterization of new chromophores with second order optical nonlinearities containing the 2-phenyl-(5,6)-nitrobenzimidazole group is reported. Starting from 2-4-[(4-N,N-dihydroxyethylamino)phenylazo]phenyl}-5(6)-nitrobenzimidazole, a combined theoretical and experimental approach, including theoretical computations of second order nonlinear optical activity (MNDO/AM1), X-ray structural analysis and

  报道了含有 2-苯基-(5,6)-硝基苯并咪唑基团的具有二阶光学非线性的新型发色团的合成和完整表征。从 2-4-[(4-N,N-dihydroxyethylamino)phenylazo]phenyl}-5(6)-nitrobenzimidazole 开始，一种理论和实验相结合的方法，包括二阶非线性光学活性 (MNDO/AM1) 的理论计算X 射线结构分析和合成策略导致相关发色团 NLO 活性的显着优化（超过 50%）。结果表明，6-硝基取代的化合物比5-硝基取代的化合物更具活性，并且通过在苯并咪唑和2-苯环之间插入碳-碳双键可以进一步提高NLO活性。计算还表明，在用吸电子基团对 6-硝基苯并咪唑的 N1 原子进行功能化后，非线性度会进一步改善。测量了 940 和 1550 之间的实验非线性（EFISH 技术，μβ/10−48 esu，λ = 1.907 μm，DMF 溶液）。(© Wiley-VCH
• 一类Tröger’s base-Schiff碱衍生物及其制备方法与应用
  申请人：江苏师范大学

  公开号：CN110627798B

  公开（公告）日：2022-04-26

  一类base‑Schiff碱衍生物，其结构通式如下式[I]所示，其由对溴苯胺、多聚甲醛、正丁基锂、对氨基苯甲酸、取代邻苯二胺等原料通过缩合反应制得。本发明的base‑Schiff碱衍生物荧光为蓝色发光，具有明显的聚集诱导发光和固态发光，部分化合物对Al3+具有识别能力，两个化合物对三阴性乳腺癌细胞和肝癌细胞一种或者两种具有良好的抑制作用，且对正常细胞的毒性较小；三种化合物对非小细胞肺癌细胞、三阴性乳腺癌细胞和肺癌细胞三种细胞一种或者多种细胞有一定程度的抑制效果。