(9ci)-1-甲基-1H-苯并咪唑-5-甲腈 | 53484-13-2

• 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: (9ci)-1-甲基-1H-苯并咪唑-5-甲腈
• 中文别名: 5-氰基-1-甲基苯并咪唑
• 英文名称: 1-methyl-1H-benzo[d]imidazole-5-carbonitrile
• 英文别名: 5-Cyano-1-methylbenzoimidazole；1-methylbenzimidazole-5-carbonitrile
• CAS: 53484-13-2
• 化学式: C₉H₇N₃
• mdl: MFCD09027482
• 分子量: 157.175
• InChiKey: PJHYDBVFHHMVCS-UHFFFAOYSA-N

物化性质

• 沸点：
  346.7±34.0 °C(Predicted)
• 密度：
  1.19±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)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

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: 5-Cyano-1-methylbenzoimidazole
Synonyms: 1-Methyl-1H-benzo[d]imidazole-5-carbonitrile

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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-Cyano-1-methylbenzoimidazole
CAS number: 53484-13-2

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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: C9H7N3
Molecular weight: 157.2

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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：

  (9ci)-1-甲基-1H-苯并咪唑-5-甲腈 在 甲酸 、 platinum(IV) oxide hydrate 作用下， 以 水 为溶剂， 以51 %的产率得到1-甲基-1H-苯并咪唑-5-甲醛
  参考文献：
  名称：

  Leucettinibs，一类 DYRK/CLK 激酶抑制剂，灵感源自海洋海绵天然产物 Leucetamine B

  摘要：

  双特异性酪氨酸磷酸化调节激酶 (DYRK) 和 cdc2 样激酶 (CLK) 最近因其在各种病理学中的重要参与而引起了人们的关注。我们在此描述了一系列源自亮氨酰胺和海洋天然产物亮氨酰胺 B 的 DYRK/CLK 抑制剂。合成了 45 种带有融合的 [6 + 5]-杂芳基亚甲基的N 2-官能化 2-氨基咪唑啉-4-酮。苯并噻唑-6-基亚甲基被选为 15 个不同杂芳基亚甲基中最有效的残基。合成并广泛表征了186 个带有苯并噻唑-6-基亚甲基的N 2-取代 2-氨基咪唑啉-4-酮，统称为 Leucettinib。鉴定出亚纳摩尔 IC 50 （DYRK1A 为 0.5-20 nM）抑制剂，并在 DYRK1A 中对一种 Leucettinib 进行建模，并与 CLK1 和较弱抑制的脱靶 CSNK2A1 共结晶。合成了 Leucettinib 的激酶失活异构体（DYRK1A 上 >3–10 μM），称为

  DOI：

  10.1021/acs.jmedchem.3c00884
• 作为产物：
  描述：

  4-氯-3-硝基苯甲腈 在 铁粉 、 对甲苯磺酸 、 calcium chloride 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (9ci)-1-甲基-1H-苯并咪唑-5-甲腈
  参考文献：
  名称：

  铑（I）催化的C–H活化的苯并咪唑的C2选择性支链烷基化

  摘要：

  在本文中，我们报道了Rh（I）/双膦/ K 3 PO 4催化体系，首次使苯并咪唑与Michael受体进行了选择性支链C–H烷基化。用N，N-二甲基丙烯酰胺进行的支化烷基化已成功地用于各种苯并咪唑的烷基化反应，这些苯并咪唑掺入了各种N-取代基，并且在芳烃的不同部位均显示出富电子和贫电子的功能。此外，通过用甲基丙烯酸乙酯进行烷基化来引入季碳。该方法还显示出可用于氮杂苯并咪唑的C 2-选择性支链烷基化。

  DOI：

  10.1021/acs.joc.7b01723

文献信息

• [EN] 2-(4-ARYL-1H-IMIDAZOL-1-YL)ANILINE COMPOUNDS<br/>[FR] COMPOSÉS 2-(4-ARYL-1H-IMIDAZOL-1-YL)ANILINE
  申请人：UNIV COLORADO REGENTS

  公开号：WO2015171951A1

  公开（公告）日：2015-11-12

  The present invention provides compounds that are useful as vaccine adjuvants and/or antitumor agents and methods for producing and using the same. In one particular aspect of the invention, compounds of the invention are of the formula (I) where R1, R2, R3 and Ar1 are those defined herein.

  本发明提供了作为疫苗佐剂和/或抗肿瘤药物有用的化合物，以及制备和使用这些化合物的方法。在本发明的一个特定方面，本发明的化合物具有以下式（I）的结构，其中R1、R2、R3和Ar1如本文所定义。
• [EN] SUBSTITUTED 4-(1-PYRROLIDINYL)PYRIMIDINE COMPOUNDS AS DIMERIZATION INHIBITORS OF NEURONAL NITRIC OXIDE SYNTHASE<br/>[FR] COMPOSÉS DE 4-(1-PYRROLIDINYL)PYRIMIDINE SUBSTITUÉS EN TANT QU'INHIBITEURS DE LA DIMÉRISATION DE L'OXYDE NITRIQUE SYNTHASE NEURONALE
  申请人：UNIV NORTHWESTERN

  公开号：WO2017214286A1

  公开（公告）日：2017-12-14

  Disclosed are compounds, pharmaceutical compositions comprising the compounds, and methods of using the compounds and pharmaceutical compositions for treating a subject in need thereof. The disclosed compounds may be described as substituted 4-(1-pyrrolidinyl)pyrimidine compounds. The disclosed compounds are shown to inhibit the activity of nitric oxide synthases (NOSs) including neuronal NOS (nNOS) by inhibiting dimerization, and as such, the disclosed compounds and pharmaceutical compositions may be utilized in methods for treating a subject having or at risk for developing a disease or disorder that is associated with nNOS activity.

  揭示了化合物、含有这些化合物的药物组合物以及使用这些化合物和药物组合物治疗需要的受试者的方法。所揭示的化合物可以描述为取代的4-(1-吡咯啉基)嘧啶化合物。所揭示的化合物被证明能通过抑制二聚化来抑制一氧化氮合酶（NOSs）的活性，包括神经元NOS（nNOS），因此，这些化合物和药物组合物可用于治疗患有或有风险发展与nNOS活性相关的疾病或紊乱的受试者的方法。
• Using Methanol as a Formaldehyde Surrogate for Sustainable Synthesis of <scp> <i>N</i> ‐Heterocycles </scp> via <scp>Manganese‐Catalyzed</scp> Dehydrogenative Cyclization
  作者：Zhihui Shao、Shanshan Yuan、Yibiao Li、Qiang Liu

  DOI：10.1002/cjoc.202100886

  日期：2022.5.15

  The development of an efficient and sustainable synthetic route for formaldehyde production from renewable feedstock, especially in combination with a subsequent transformation to straightforwardly construct valuable chemicals, is highly desirable. Herein, we report a novel manganese-catalyzed dehydrogenative cyclization of methanol as a formaldehyde surrogate with a variety of dinucleophiles for facile

  开发一种高效且可持续的从可再生原料生产甲醛的合成路线，尤其是结合随后的转化以直接构建有价值的化学品是非常可取的。在此，我们报告了一种新型的锰催化甲醇脱氢环化反应，作为甲醛替代物，其具有多种亲核试剂，可方便地合成N-杂环化合物。通过催化甲醇脱氢原位产生的甲醛可以被多种双亲核试剂选择性地捕获，以避免几种可能的副反应。这种转化的实用性通过其成功应用于合成13 C-标记的N-杂环使用13 CH 3 OH 作为容易获得的13 C-同位素试剂。
• [EN] FACTOR IXA INHIBITORS<br/>[FR] INHIBITEURS DU FACTEUR IXA
  申请人：MERCK SHARP & DOHME

  公开号：WO2015160636A1

  公开（公告）日：2015-10-22

  In its many embodiments, the present invention provides a novel class of benzamide compounds represented by Formula (I) or pharmaceutically acceptable salts or solvates thereof, or pharmaceutical compositions comprising one or more said compounds or pharmaceutically acceptable salts or solvates thereof, and methods for using said compounds or pharmaceutically acceptable salts or solvates thereof for treating or preventing a thromboses, embolisms, hypercoagulability or fibrotic changes.

  在其多种实施方式中，本发明提供了一类新型的苯甲酰胺化合物，其由式（I）表示，或者其药用可接受的盐或溶剂，或者包含一种或多种所述化合物或其药用可接受的盐或溶剂的药物组合物，并提供了使用所述化合物或其药用可接受的盐或溶剂来治疗或预防血栓、栓塞、高凝血性或纤维变化的方法。
• [EN] AGRICULTURAL CHEMICALS<br/>[FR] PRODUITS CHIMIQUES AGRICOLES
  申请人：GLOBACHEM NV

  公开号：WO2019141972A1

  公开（公告）日：2019-07-25

  The present invention relates to benzimidazole and benzotriazole compounds which are of use in the field of agriculture as fungicides.

  本发明涉及苯并咪唑和苯并三唑化合物，在农业领域作为杀菌剂使用。