1H-苯并咪唑-6-羧酸乙酯 | 58842-61-8

• 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-6-羧酸乙酯
• 中文别名: 1H-苯并咪唑-5-羧酸乙酯(9ci)
• 英文名称: benzimidazole-5-carboxylic acid ethyl ester
• 英文别名: ethyl benzimidazole-5-carboxylate；ethyl 1H-benzimidazole-5-carboxylate；ethyl 3H-benzimidazole-5-carboxylate
• CAS: 58842-61-8
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: HUOIDCCHUGUZQS-UHFFFAOYSA-N

物化性质

• 密度：
  1.272±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl benzimidazole-5-carboxylate
Synonyms: Ethyl 1H-1,3-benzodiazole-5-carboxylate

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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: Ethyl benzimidazole-5-carboxylate
CAS number: 58842-61-8

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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: 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-6-羧酸乙酯 在 盐酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.5h， 生成 N'-[(2-hydroxy-3,5-di-tert-butyl)phenylmethylene]-1H-benzo[d]imidazole-6-formhydrazide hydrochloride
  参考文献：
  名称：

  SUBSTITUTED HYDRAZIDE COMPOUNDS AND USE THEREOF

  摘要：

  本发明涉及通式I所示的取代肼化合物，包括几何异构体、药学上可接受的盐、水合物、溶剂合物或前药，以及其使用，其中取代基Ar和R的含义与说明中给出的相同。本发明还涉及通式I化合物在制备用于治疗和/或预防癌症和其他增殖性疾病的药物中的使用。

  公开号：

  US20120142921A1
• 作为产物：
  描述：

  3,4-二氨基苯甲酸 在 硫酸 作用下， 反应 3.0h， 生成 1H-苯并咪唑-6-羧酸乙酯
  参考文献：
  名称：

  SUBSTITUTED HYDRAZIDE COMPOUNDS AND USE THEREOF

  摘要：

  本发明涉及通式I所示的取代肼化合物，包括几何异构体、药学上可接受的盐、水合物、溶剂合物或前药，以及其使用，其中取代基Ar和R的含义与说明中给出的相同。本发明还涉及通式I化合物在制备用于治疗和/或预防癌症和其他增殖性疾病的药物中的使用。

  公开号：

  US20120142921A1

文献信息

• Thrombin inhibitors
  申请人：Merck & Co., Inc.

  公开号：US06610692B1

  公开（公告）日：2003-08-26

  Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: or a pharmaceutically acceptable salt thereof, wherein b is NY or O; c is CY2 or N; d is CY3 or N; e is CY4 or N; f is CY5 or N; g is CY6 or N; Y4, Y5, and Y6 are independently hydrogen, C1-4 alkyl, or halogen; Y1 and Y2 are independently hydrogen, C1-4 alkyl, C3-7 cycloalkyl, halogen, NH2, OH or C1-4 alkoxy, and Y3 is hydrogen, C1-4 alkyl, C3-7 cycloalkyl, halogen, —CN, NH2, OH or C1-4 alkoxy; A is and W, W1, R1, R3, R4, R5, X and Z are defined in the specification.

  发明的化合物在抑制凝血酶和相关血栓闭塞方面具有以下结构：或其药学上可接受的盐，其中b为NY或O；c为CY2或N；d为CY3或N；e为CY4或N；f为CY5或N；g为CY6或N；Y4、Y5和Y6独立地为氢、C1-4烷基或卤素；Y1和Y2独立地为氢、C1-4烷基、C3-7环烷基、卤素、NH2、OH或C1-4烷氧基，Y3为氢、C1-4烷基、C3-7环烷基、卤素、—CN、NH2、OH或C1-4烷氧基；A为，并且W、W1、R1、R3、R4、R5、X和Z在规范中有定义。
• Cyclization of o-phenylenediamines by CO₂in the presence of H₂for the synthesis of benzimidazoles
  作者：Bo Yu、Hongye Zhang、Yanfei Zhao、Sha Chen、Jilei Xu、Changliang Huang、Zhimin Liu

  DOI：10.1039/c2gc36517k

  日期：——

  The cyclization of o-phenylenediamines by CO2 in the presence of H2 was presented to directly synthesize benzimidazoles, and a series of benzimidazoles were obtained in excellent yields using RuCl2(dppe)2 as the catalyst.

  在H2存在下，通过CO2使邻苯二胺环化，可直接合成苯并咪唑，使用RuCl2(dppe)2作为催化剂，一系列苯并咪唑化合物以优异的产率获得。
• Copper-Catalyzed Inter/Intramolecular <i>N</i>-Alkenylation of Benzimidazoles via Tandem Processes Involving Selectively Mild Iodination of sp³ C–H Bond at α-Position of Ester
  作者：Ting-Ting Lai、Dan Xie、Cheng-He Zhou、Gui-Xin Cai

  DOI：10.1021/acs.joc.6b01465

  日期：2016.10.7

  copper catalyst. Both intermolecular and intramolecular reactions included tandem processes, in which selective iodination of sp3 C–H bond at the α-position of ester under mild conditions was demonstrated for the first time. Tandem reactions involving sp3 C–H activation via α-iodo ester intermediate under copper catalysis efficiently provided more than 20 novel azole compounds, and free radicals were not

  N /烯基苯并咪唑的sp 2 C–N键形成的分子间/分子间方法是在与铜催化剂缔合的碘化物阴离子存在下完成的。分子间和分子内反应都包括串联过程，其中首次证明了在温和条件下，在酯的α-位上sp 3 C–H键的选择性碘化。在铜催化下，通过α-碘代酯中间体通过sp 3 C–H激活的串联反应有效地提供了20多种新型唑化合物，并且自由基不参与该转化。
• Cobalt-catalyzed synthesis of N-containing heterocycles <i>via</i> cyclization of <i>ortho</i>-substituted anilines with CO₂/H₂
  作者：Zhengang Ke、Bo Yu、Huan Wang、Junfeng Xiang、Juanjuan Han、Yunyan Wu、Zhenghui Liu、Peng Yang、Zhimin Liu

  DOI：10.1039/c9gc00095j

  日期：——

  The CO2-involved synthesis of chemicals is of great significance from the green and sustainable chemistry viewpoint. Herein, we report a non-noble metal catalytic system composed of CoF2, CsF and P(CH2CH2PPh2)3 (denoted as PP3) for the synthesis of N-containing heterocycles from ortho-substituted anilines and CO2/H2. Mechanism investigation indicates that [Co(PP3)H(CO2)]+ is a catalytically active

  从绿色和可持续的化学观点来看，涉及CO 2的化学合成具有重要意义。本文中，我们报道了由CoF 2，CsF和P（CH 2 CH 2 PPh 2）3（表示为P P 3）组成的非贵金属催化体系，用于由邻位取代的苯胺和CO合成含氮杂环2 / H 2。机理研究表明[Co（P P 3）H（CO 2）] +是在工作条件下具有催化活性的中间体；CsF和CsF在通过氢键相互作用活化邻位取代的苯胺中起重要作用，从而促进最终产物的形成。该催化体系是高效的，并且允许宽范围的邻位取代的苯胺，以及优异的官能团耐受性，以良好至优异的产率提供各种含氮杂环。
• A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides
  作者：Wanwan Sun、Xiaobei Chen、Ying Hu、Huihui Geng、Yuanrui Jiang、Yuxin Zhou、Wenjing Zhu、Min Hu、Haohua Hu、Xingyi Wang、Xinli Wang、Shilei Zhang、Yanwei Hu

  DOI：10.1016/j.tetlet.2020.152442

  日期：2020.10

  features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.

  据报道，由NaH介导的各种Ts保护的吲哚，氮杂杂环，苯胺和二苄基胺的解毒反应。该方法试剂便宜，操作方便，反应条件温和，底物范围广。此外，这项研究表明，由于可能发生不利的脱甲苯基作用，因此应控制在含氮化合物以NaH为碱的含氮化合物甲苯磺酸化反应中NaH的负载量。