4-(3,5-二甲基吡唑-1-基)苯硼酸频那醇酯 | 937796-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(3,5-二甲基吡唑-1-基)苯硼酸频那醇酯
• 英文名称: 3,5-Dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole
• 英文别名: 3,5-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrazole
• CAS: 937796-06-0
• 化学式: C₁₇H₂₃BN₂O₂
• mdl: MFCD09879979
• 分子量: 298.193
• InChiKey: SERWCEBXGSSDRB-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112°C
• 沸点：
  407.1±33.0 °C(Predicted)
• 密度：
  1.06±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)：
  4.04
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P310+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(3,5-Dimethylpyrazol-1-yl)phenylboronic acid, pinacol ester
Synonyms: 3,5-Dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1h-pyrazole

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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: 4-(3,5-Dimethylpyrazol-1-yl)phenylboronic acid, pinacol ester
CAS number: 937796-06-0

---

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: C17H23BN2O2
Molecular weight: 298.2

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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.

---

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-(3,5-二甲基吡唑-1-基)苯硼酸频那醇酯 在 吡啶 、 potassium [¹⁸F]fluoride 、 potassium trifluoromethansulfonate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成
  参考文献：
  名称：

  快速放射化学探索的高通量实验方法的开发

  摘要：

  正电子发射断层扫描是一种广泛用于研究生理过程的成像平台。尽管放射性标记的现代合成方法不断涌现，但这些反应的优化仍然主要依赖于低效的一次一因子方法。高通量实验 (HTE) 已被证明是优化化学合成许多领域反应的有效方法。然而，迄今为止，HTE 很少应用于放射化学。这主要是因为常见放射性同位素的寿命较短，这对使用标准设备和工作流程进行高效平行反应设置和分析提出了重大挑战。在此，我们展示了一种有效的 HTE 工作流程，并将其应用于药物相关硼酸酯底物的铜介导的放射性氟化的优化。该工作流程利用商业设备，并允许快速分析反应以优化反应，使用药学相关的芳基硼酸盐进行放射性氟化探索化学空间，并构建大型放射化学数据集。

  DOI：

  10.1021/jacs.3c14822
• 作为产物：
  描述：

  4-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)氯苯 在 [Pd(1-MeNAP)(^tBuBrettPhos)Br] 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 22.0h， 生成 4-(3,5-二甲基吡唑-1-基)苯硼酸频那醇酯
  参考文献：
  名称：

  Pd-甲基萘基-tBuBrettPhos 配合物作为氨和肼单芳基化的高效选择性催化剂

  摘要：

  只有少数空间拥挤的配体促进钯催化的氨和肼的选择性单芳基化。我们在此证明，带有此类配体的钯预催化剂的形成是这些反应中的限制因素，并且我们提出了实验室稳定的 Pd-甲基萘基 (MeNAP) -t BuBrettPhos 络合物作为有效的催化剂。 X射线和光谱分析表明，配体的联芳基系统在配合物形成过程中可逆地插入Pd-(MeNAP)C键中。 MeNAP 复合物的性能被证明是其干净形成和快速激活的结果。 32 苯胺和芳基肼的合成证明了它们的制备实用性。

  DOI：

  10.1021/acscatal.4c02624

文献信息

• Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods
  作者：Peter S. Kutchukian、James F. Dropinski、Kevin D. Dykstra、Bing Li、Daniel A. DiRocco、Eric C. Streckfuss、Louis-Charles Campeau、Tim Cernak、Petr Vachal、Ian W. Davies、Shane W. Krska、Spencer D. Dreher

  DOI：10.1039/c5sc04751j

  日期：——

  We report a standardized complex molecule diagnostic approach using collections of relevant drug-like molecules which we call chemistry informer libraries.

  我们报告了一种标准化的复杂分子诊断方法，使用我们称之为化学信息库的相关类药物分子集合。
• Synthesis of HDAC Inhibitor Libraries via Microscale Workflow
  作者：Kevin D. Dykstra、Eric Streckfuss、Min Liu、Jian Liu、Younong Yu、Ming Wang、Joseph A. Kozlowski、Robert W. Myers、Alexei V. Buevich、Milana M. Maletic、Petr Vachal、Shane W. Krska

  DOI：10.1021/acsmedchemlett.0c00596

  日期：2021.3.11
• Development of High-Throughput Experimentation Approaches for Rapid Radiochemical Exploration
  作者：E. William Webb、Kevin Cheng、Wade P. Winton、Brandon J.C. Klein、Gregory D. Bowden、Mami Horikawa、S. Wendy Liu、Jay S. Wright、Stefan Verhoog、Dipannita Kalyani、Michael Wismer、Shane W. Krska、Melanie S. Sanford、Peter J.H. Scott

  DOI：10.1021/jacs.3c14822

  日期：2024.4.17

  HTE workflow and apply it to the optimization of copper-mediated radiofluorination of pharmaceutically relevant boronate ester substrates. The workflow utilizes commercial equipment and allows for rapid analysis of reactions for optimizing reactions, exploring chemical space using pharmaceutically relevant aryl boronates for radiofluorinations, and constructing large radiochemistry data sets.

  正电子发射断层扫描是一种广泛用于研究生理过程的成像平台。尽管放射性标记的现代合成方法不断涌现，但这些反应的优化仍然主要依赖于低效的一次一因子方法。高通量实验 (HTE) 已被证明是优化化学合成许多领域反应的有效方法。然而，迄今为止，HTE 很少应用于放射化学。这主要是因为常见放射性同位素的寿命较短，这对使用标准设备和工作流程进行高效平行反应设置和分析提出了重大挑战。在此，我们展示了一种有效的 HTE 工作流程，并将其应用于药物相关硼酸酯底物的铜介导的放射性氟化的优化。该工作流程利用商业设备，并允许快速分析反应以优化反应，使用药学相关的芳基硼酸盐进行放射性氟化探索化学空间，并构建大型放射化学数据集。
• 10.1021/acscatal.4c02624
  作者：Xue, Bingxiang、Papp, Florian、Yang, Muyang、Shen, Jie、Doppiu, Angelino、Gooßen, Lukas J.

  DOI：10.1021/acscatal.4c02624

  日期：——

  Only a few sterically crowded ligands promote palladium-catalyzed, selective monoarylations of ammonia and hydrazine. We herein demonstrate that the formation of palladium precatalysts bearing such ligands is the limiting factor in these reactions, and we present bench-stable, Pd-methylnaphthyl (MeNAP)-tBuBrettPhos complexes as effective catalysts. X-ray and spectroscopic analyses have revealed that

  只有少数空间拥挤的配体促进钯催化的氨和肼的选择性单芳基化。我们在此证明，带有此类配体的钯预催化剂的形成是这些反应中的限制因素，并且我们提出了实验室稳定的 Pd-甲基萘基 (MeNAP) -t BuBrettPhos 络合物作为有效的催化剂。 X射线和光谱分析表明，配体的联芳基系统在配合物形成过程中可逆地插入Pd-(MeNAP)C键中。 MeNAP 复合物的性能被证明是其干净形成和快速激活的结果。 32 苯胺和芳基肼的合成证明了它们的制备实用性。