1H-苯并咪唑-2-羧酸乙酯 | 1865-09-4

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 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: 1H-苯并咪唑-2-羧酸乙酯
• 英文名称: ethyl 1H-benzimidazole-2-carboxylate
• 英文别名: ethyl 1H-benzo[d]imidazole-2-carboxylate；ethyl benzimidazole-2-carboxylate；ethyl 2-benzimidazole carboxylate；Benzimidazol-carbonsaeure-(2)-ethylester
• CAS: 1865-09-4
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: NMYSVCYIPOCLEC-UHFFFAOYSA-N

物化性质

• 熔点：
  212.7-213.7 °C
• 沸点：
  350.0±25.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1H-Benzoimidazole-2-carboxylic acid ethyl ester
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: 1H-Benzoimidazole-2-carboxylic acid ethyl ester
CAS number: 1865-09-4

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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, refrigerated.
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: C10H10N2O2
Molecular weight: 190.2

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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：

  1H-苯并咪唑-2-羧酸乙酯 在 水 、 二甲基亚砜 作用下， 反应 3.0h， 生成 N,N'-二甲基苯并咪唑鎓碘化物
  参考文献：
  名称：

  Glowczyk, Joanna; Serafin, Barbara, Polish Journal of Chemistry, 1984, vol. 58, # 1-3, p. 149 - 156

  摘要：

  DOI：
• 作为产物：
  描述：

  苯并呋咱 在 氢氧化钾 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 15.0h， 生成 1H-苯并咪唑-2-羧酸乙酯
  参考文献：
  名称：

  一些N-（2-苯并咪唑基）-α-氨基酯及其N-氧化物的合成及光谱性质

  摘要：

  制备了一系列新的N-（2-苯并咪唑）（S）-α-氨基酯和相应的N-氧化物，并讨论了它们的光谱数据。任一系列的脂族和芳族氨基酯衍生物的CD光谱均显示出所观察到的Cotton效应（CE）谱带的符号反转。由于构象异构现象的差异，这种按摩疗法行为被合理化了。

  DOI：

  10.1002/jhet.5570240131

文献信息

• An efficient one-pot two catalyst system in the construction of 2-substituted benzimidazoles: synthesis of benzimidazo[1,2-c]quinazolines
  作者：Cristina Cimarelli、Matteo Di Nicola、Simone Diomedi、Riccardo Giovannini、Dieter Hamprecht、Roberta Properzi、Federico Sorana、Enrico Marcantoni

  DOI：10.1039/c5ob01777g

  日期：——

  cyclo-dehydrogenation of aniline Schiff's bases, generated in situ from the condensation of 1,2-phenylenediamine and aldehydes, followed by the oxidation with iodine, which works as a hydrogen sponge. Mild reaction conditions, good to excellent yields, and clean reactions make the procedure a useful contribution to the synthesis of biologically active fused heterocycles containing benzimidazoquinazolines.

  苯并咪唑核心是大量天然产物和具有药理活性的小分子的共同组成部分。新型苯并咪唑衍生物的合成仍然是医学研究的主要重点。在继续努力实现有机转化的Ce（III）催化剂方面，我们首次观察到碘离子和铜阳离子在选择性形成原型2取代的苯并咪唑类化合物中活化CeCl 3 ·7H 2 O的活性。一锅法CeCl 3 ·7H 2 O–CuI催化系统程序包括原位生成的苯胺席夫碱的环脱氢1，2-苯二胺和醛的缩合反应，然后用碘氧化，碘作为氢海绵。温和的反应条件，良好或优异的收率以及干净的反应使该方法对合成含有苯并咪唑并喹唑啉类的生物活性稠合杂环作出了有益的贡献。
• [EN] INHIBITORS OF BRUTON'S TYROSINE KINASE<br/>[FR] INHIBITEURS DE LA TYROSINE KINASE DE BRUTON
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015086636A1

  公开（公告）日：2015-06-18

  This application discloses compounds according to generic Formula (I): wherein all variables are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are useful for the treatment of oncological, auto-immune, and inflammatory diseases caused by aberrant B-cell activation. Also disclosed are compositions containing compounds of Formula I and at least one carrier, diluent or excipient.

  该应用程序根据通用公式（I）披露化合物：其中所有变量的定义如本文所述，这些化合物抑制Btk。本文披露的化合物对调节Btk的活性并治疗与过度Btk活性相关的疾病有用。这些化合物对于治疗由异常B细胞活化引起的肿瘤学、自身免疫和炎症性疾病是有用的。还披露了含有公式I化合物和至少一种载体、稀释剂或赋形剂的组合物。
• [EN] ADENOSINE RECEPTOR BINDING COMPOUNDS<br/>[FR] COMPOSÉS SE LIANT AU RÉCEPTEUR DE L'ADÉNOSINE
  申请人：NIKANG THERAPEUTICS INC

  公开号：WO2020014332A1

  公开（公告）日：2020-01-16

  The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.

  本发明涉及化学式（I）的药物化合物和组合物，以及使用这些化合物和组合物进行治疗的方法，特别是用于治疗和/或预防增殖性疾病，如癌症。如本文进一步描述的化合物（I）被显示为腺苷A2A受体的调节剂，并表现出抗增殖活性。因此，这些化合物对于治疗增殖性疾病如癌症以及其他与腺苷受体相关的疾病条件包括炎症性疾病、肾脏疾病、糖尿病、血管疾病、肺部疾病或自身免疫疾病是有用的。
• Reactions of hydroxylamines with ethyl cyanoformate. preparation of aminonitrones and their synthetic applications.
  作者：Paula S. Branco、Sundaresan Prabhakar、Ana M. Lobo、David J. Williams

  DOI：10.1016/s0040-4020(01)88224-7

  日期：1992.1

  The reaction of hydroxylamines with ethyl cyanoformate leads to the formation of carbethoxyamino nitrones . UV spectroscopy provided information that suggested the nitrone structure for these compounds in solution. X-ray analysis of confirmed that it exists entirely in the nitrone form in the solid state. These nitrones are shown to be excellent starting materials for a variety of nitrogen containg

  羟胺与氰基甲酸乙酯的反应导致形成乙氧基氨基硝酮。紫外光谱提供的信息表明溶液中这些化合物的硝酮结构。的X射线分析证实其完全以固态存在于硝酮形式。这些硝酮被证明是各种含氮化合物（即咪唑，苯并咪唑，苯并咪唑酮，恶二唑酮，N-芳基idine啶和喹喔啉）的极佳原料。
• Synthesis and Biological Evaluation of Novel N' (4-aryloxybenzylidene)- 1H-Benzimidazole-2 Carbohydrazide Derivatives as Anti-Tubercular Agents
  作者：Afsar Siddiki、Vinod Bairwa、Vikas Telvekar

  DOI：10.2174/1386207317666140314092412

  日期：2014.7.16

  A series of structurally novel, (E)-N'-(4-aryloxybenzylidene)-1H-benzimidazole-2-carbohydrazide derivatives were synthesized by molecular hybridization technique. All these compounds were evaluated against Mycobacterium tuberculosis H37Rv strains using Resazurin Microtiter assay (REMA) method. These compounds showed good antituberculosis activity with minimum inhibitory concentration (MIC) value of the range of 1.5-25 µg/mL.

  通过分子杂交技术合成了一系列结构新颖的（E）-N'-(4-芳氧基苄叉)-1H-苯并咪唑-2-羧酰肼衍生物。这些化合物使用刃天青微量滴定法（REMA）对结核分枝杆菌H37Rv株进行了评估。这些化合物显示出良好的抗结核活性，最低抑制浓度（MIC）值范围为1.5-25 µg/mL。