5-硝基-2-(三氟甲基)-1H-苯并咪唑 | 327-19-5

• 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: 5-硝基-2-(三氟甲基)-1H-苯并咪唑
• 中文别名: 5-硝基-2-(三氟甲基)苯并咪唑；6-硝基-2-(三氟甲基)-1H-苯并咪唑；苯并咪唑,5-硝基-2-(三氟甲基)-
• 英文名称: 5-nitro-2-(trifluoromethyl)-1H-benzo[d]imidazole
• CAS: 327-19-5
• 化学式: C₈H₄F₃N₃O₂
• mdl: MFCD00458655
• 分子量: 231.134
• InChiKey: FEJRBJIEEALTTL-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Nitro-2-(trifluoromethyl)-1H-benzimidazole
Synonyms: 5-Nitro-2-(trifluoromethyl)-3H-1,3-benzodiazole

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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: 5-Nitro-2-(trifluoromethyl)-1H-benzimidazole
CAS number: 327-19-5

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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: C8H4F3N3O2
Molecular weight: 231.1

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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, hydrogen fluoride.

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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：

  5-硝基-2-(三氟甲基)-1H-苯并咪唑 以64%的产率得到
  参考文献：
  名称：

  MOORES, I. G.;SMALLEY, R. K.;SUSCHITZKY, H., J. FLUOR. CHEM., 1982, 20, N 5, 573-580

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(三氟甲基)苯并咪唑 在 硝酸 作用下， 生成 5-硝基-2-(三氟甲基)-1H-苯并咪唑
  参考文献：
  名称：

  2-（全氟烷基）-苯并咪唑类中全氟烷基的反应性

  摘要：

  DOI：

  10.1039/jr9550000534

文献信息

• Baker’s Yeast-Mediated Regioselective Reduction of 2,4-Dinitroacylanilines: Synthesis of 2-Substituted 6-Nitrobenzimidazoles
  作者：Arturo Navarro-Ocaña、Luís F. Olguín、Manuel Jiménez-Estrada、Eduardo Bárzana

  DOI：10.1055/s-2004-837203

  日期：——

  Several 2,4-dinitro-N-acylanilines were regioselectively reduced at the C-2 position by baker's yeast in slightly basic media (pH = 7.5) to afford 2-amino-4-nitroacylanilines, which were then cyclized under acidic conditions to the corresponding 2-substituted-6-nitrobenzimidazoles. The benzimidazoles thus obtained can be employed as precursors for bioactive derivatives.

  几种 2,4-二硝基-N-酰基苯胺在微碱性介质（pH = 7.5）中被面包酵母在 C-2 位置区域选择性还原，得到 2-氨基-4-硝基酰基苯胺，然后在酸性条件下环化为相应的 2-取代-6-硝基苯并咪唑。由此获得的苯并咪唑可用作生物活性衍生物的前体。
• Fe(OTf) 3 -catalyzed practical synthesis of 2-trifluoromethylarylimidazoles from o -arylenediamines and hexafluoroacetylacetone
  作者：Yanmei Zhou、Guanshuo Shen、Yuebo Sui、Haifeng Zhou

  DOI：10.1016/j.tetlet.2016.06.086

  日期：2016.7

  An iron-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles through condensation of o-arylenediamines and hexafluoroacetylacetone followed by intramolecular addition and C–C bond cleavage in one-pot has been developed. A series of title compounds were obtained with up to 99% yield. This method is quite practical and suitable for scalable preparation due to simple experimental procedure

  已经开发出铁催化的实际合成方法，即通过邻芳基二胺和六氟乙酰丙酮的缩合，然后分子内加成和一锅中C–C键的裂解，合成2-三氟甲基芳基咪唑。获得了一系列标题化合物，产率高达99％。由于简单的实验程序和容易获得的试剂，该方法非常实用并且适合于可扩展的制备。
• Cinnamide derived pyrimidine-benzimidazole hybrids as tubulin inhibitors: Synthesis, in silico and cell growth inhibition studies
  作者：Sravani Sana、Velma Ganga Reddy、T. Srinivasa Reddy、Ramya Tokala、Rahul Kumar、Suresh K. Bhargava、Nagula Shankaraiah

  DOI：10.1016/j.bioorg.2021.104765

  日期：2021.5

  An approach in modern medicinal chemistry to discover novel bioactive compounds is by mimicking diverse complementary pharmacophores. In extension of this strategy, a new class of piperazine-linked cinnamide derivatives of benzimidazole-pyrimidine hybrids have been designed and synthesized. Their in vitro cytotoxicity profiles were explored on selected human cancer cell lines. Specifically, structural

  现代药物化学中发现新型生物活性化合物的一种方法是模拟不同的互补药效团。作为该策略的延伸，设计并合成了一类新的苯并咪唑-嘧啶杂化物的哌嗪连接肉桂酰胺衍生物。在选定的人类癌细胞系上探索了它们的体外细胞毒性特征。具体而言，目标杂交体与微管蛋白-DAMA-秋水仙碱和微管蛋白-诺考达唑复合物的结构比较暴露了苯并咪唑环进入α的深层位置。T5循环。所有合成的化合物都被证明对不同的癌细胞系具有适度的细胞毒性。苯并咪唑-嘧啶系列的胺接头显示出最大的细胞毒性，对 A549（肺癌）细胞系具有特异性。该系列中最有效的化合物是18i，它以 2.21–7.29 µM 的微摩尔浓度抑制癌细胞生长。流式细胞术研究表明，18i抑制细胞周期 G2/M 期的细胞。18i的强效抗肿瘤活性源于增强的微管破坏，与诺考达唑对β-微管蛋白抗体的破坏程度相似，使用免疫荧光染色进行了探索。最活跃的化合物18i还抑制微管蛋白聚合，IC 50为
• [EN] 1-CYANO-PYRROLIDINE DERIVATIVES AS INHIBITORS OF USP30.<br/>[FR] DÉRIVÉS DE 1-CYANO-PYRROLIDINE EN TANT QU'INHIBITEURS DE L'USP 30
  申请人：MISSION THERAPEUTICS LTD

  公开号：WO2017093718A1

  公开（公告）日：2017-06-08

  The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylatingenzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C- terminal hydrolase 30 or Ubiquitin Specific Peptidase 30 (USP30). The invention further relates to the use of DUB inhibitors in the treatment of conditions involving mitochondrial dysfunction and cancer. Compounds of the invention include compounds having the formula (I) (I) or a pharmaceutically acceptable salt thereof, wherein R1, R 2, R 3, m, L and X are as defined herein.

  本发明涉及新颖化合物和制备去泛素酶（DUBs）抑制剂的方法。具体而言，本发明涉及抑制泛素C-末端水解酶30或泛素特异性肽酶30（USP30）。本发明还涉及在治疗涉及线粒体功能障碍和癌症的疾病中使用DUB抑制剂。本发明的化合物包括具有以下结构式（I）的化合物或其药用盐，其中R1、R2、R3、m、L和X如本文所定义。
• 2-Trihalogenomethylbenzazoles. Part I. Formation
  作者：G. Holan、E. L. Samuel、B. C. Ennis、R. W. Hinde

  DOI：10.1039/j39670000020

  日期：——

  Methods of preparation of 2-trihalogenomethyl-benzimidazoles, -benzothiazoles, and -benzoxazoles have been investigated. It has been shown that the reaction of the mono-salts of o-phenylenediamines, o-aminophenols, and o-aminothiophenols with trichloroacetonitrile or trichloroacetimidate esters affords 2-trichloromethyl substituted benzimidazoles, benzoxazoles, and benzothiazoles. This method has been

  已经研究了2-三卤代甲基-苯并咪唑，-苯并噻唑和-苯并恶唑的制备方法。它已经显示出的单盐的反应Ó苯二胺类，ø氨基苯酚，和ö -aminothiophenols与三氯乙腈或三氯乙酰亚胺酯，得到2-三氯取代的苯并咪唑，苯并恶唑，苯并噻唑和。该方法已扩展到2-三氯甲基-2-偶氮啉的制备。还描述了制备2,2'-联苯并咪唑基的通用方法。

表征谱图