2-甲基-1H-苯并咪唑-5-硼酸频那醇酯 | 1314216-34-6

• 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: 2-甲基-1H-苯并咪唑-5-硼酸频那醇酯
• 中文别名: 2-甲基-1H-苯并咪唑-5-硼酸频哪醇酯
• 英文名称: methylbenzimidazole-5-boronic pinacol ester
• 英文别名: 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole；2-Methyl-1H-benzimidazole-5-boronic acid pinacol ester；2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole
• CAS: 1314216-34-6
• 化学式: C₁₄H₁₉BN₂O₂
• 分子量: 258.128
• InChiKey: CPQGLMCLTALRHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methyl-1h-benzimidazole-5-boronic acid pinacol 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: 2-Methyl-1h-benzimidazole-5-boronic acid pinacol ester
CAS number: 1314216-34-6

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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: C14H19BN2O2
Molecular weight: 258.1

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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.

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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-(2-chloro-6-(methylsulfonylmethyl)pyrimidin-4-yl)morpholine 、 2-甲基-1H-苯并咪唑-5-硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2-methyl-5-[4-(methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidin-2-yl]-1H-benzoimidazole
  参考文献：
  名称：

  WO2007/80382

  摘要：

  公开号：
• 作为产物：
  描述：

  2-甲基-5-溴苯并咪唑 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 2-甲基-1H-苯并咪唑-5-硼酸频那醇酯
  参考文献：
  名称：

  WO2007/80382

  摘要：

  公开号：

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET PROCÉDÉS D'UTILISATION
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2015058084A1

  公开（公告）日：2015-04-23

  The present application discloses compounds that are inhibitors of Btk, compounds that are inhibitors of ΡΒΚδ, and compounds that are dual inhibitors of both Btk and PI3Kδ. Also described are methods for synthesizing such inhibitors and methods for using such inhibitors for the treatment of diseases wherein inhibition of Btk and PI3Kδ provides a therapeutic benefit to a patient having the disease.

  本申请公开了抑制Btk的化合物、抑制ΡΒΚδ的化合物，以及既是Btk又是PI3Kδ的双重抑制剂的化合物。还描述了合成这些抑制剂的方法，以及利用这些抑制剂治疗疾病的方法，其中抑制Btk和PI3Kδ对患有该疾病的患者提供治疗益处。
• HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS
  申请人：GiraFpharma LLC

  公开号：US20190023666A1

  公开（公告）日：2019-01-24

  Aminopyrazine compounds as modulators of an adenosine receptor are provided. The compounds may find use as therapeutic agents for the treatment of diseases mediated through a G-protein-coupled receptor signaling pathway and may find particular use in oncology.

  提供了氨基吡嗪化合物作为腺苷受体的调节剂。这些化合物可能作为治疗经由G蛋白偶联受体信号通路介导的疾病的治疗剂，并且可能在肿瘤学中发挥特定作用。
• Iridium-Catalyzed C–H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism
  作者：Matthew A. Larsen、John F. Hartwig

  DOI：10.1021/ja412563e

  日期：2014.3.19

  from the olefin-bound complex observed during arene borylation to a species containing a bound heteroarene, leading to catalyst deactivation. Studies on the origins of the observed regioselectivity show that borylation occurs distal to N-H bonds due to rapid N-H borylation, creating an unfavorable steric environment for borylation adjacent to these bonds. Computational studies and mechanistic studies show

  报道了铱催化杂芳烃的 CH 硼化的研究。发现几种含有多个杂原子的杂芳烃适合由铱 (I) 前体和四甲基菲咯啉的组合催化的 CH 硼化。对反应范围的研究导致了预测硼化的区域选择性的强大规则的发展，其中最重要的是硼化发生在氮原子的远端。报告了原位形成的杂芳基硼酸酯的一锅官能化，证明了所报告的方法对合成复杂杂芳基结构的有用性。还展示了这种方法在生物活性化合物的合成和后期功能化中的应用。机理研究表明，碱性杂芳烃可以与催化剂结合，并将在芳烃硼化过程中观察到的烯烃结合复合物的静止状态改变为含有结合杂芳烃的物质，从​​而导致催化剂失活。对观察到的区域选择性起源的研究表明，由于快速的 NH 硼酸化，硼酸化发生在 NH 键的远端，为与这些键相邻的硼酸化创造了不利的空间环境。计算研究和机理研究表明，与碱性氮相邻的 CH 键缺乏可观察到的硼化并不是在 CH 活化之前与庞大的路易斯酸配位的结果，
• Triaryl Benzimidazoles as a New Class of Antibacterial Agents against Resistant Pathogenic Microorganisms
  作者：Pietro Picconi、Charlotte Hind、Shirin Jamshidi、Kazi Nahar、Melanie Clifford、Matthew E. Wand、J. Mark Sutton、Khondaker Miraz Rahman

  DOI：10.1021/acs.jmedchem.7b00108

  日期：2017.7.27

  A new class of nontoxic triaryl benzimidazole compounds, derived from existing classes of DNA minor groove binders, were designed, synthesized, and evaluated for their antibacterial activity against multidrug resistant (MDR) Gram-positive and Gram-negative species. Molecular modeling experiments suggest that the newly synthesized class cannot be accommodated within the minor groove of DNA due to a

  一种新的无毒三芳基苯并咪唑化合物，源自现有的 DNA 小沟结合剂，被设计、合成并评估了它们对多药耐药 (MDR) 革兰氏阳性和革兰氏阴性菌的抗菌活性。分子建模实验表明，由于分子形状的变化，新合成的类不能容纳在 DNA 的小沟内。化合物 8、13和14被发现是该系列中最活跃的，对 MDR 葡萄球菌和肠球菌的 MIC 范围为0.5–4 μg / mL。化合物13显示对 MDR 革兰氏阴性菌株的中等活性，MIC 在 16-32 μg/mL 范围内。活性化合物显示出杀菌作用模式，并且机制研究表明抑制细菌旋转酶是该化学类别的作用机制 (MOA)。MOA 得到分子建模研究的进一步支持。
• WO2007/80382
  申请人：——

  公开号：——

  公开（公告）日：——