4-(2-吡啶基)苯硼酸频哪醇酯 | 908350-80-1

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸/亚磺酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-(2-吡啶基)苯硼酸频哪醇酯
• 英文名称: 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine
• 英文别名: 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine
• CAS: 908350-80-1
• 化学式: C₁₇H₂₀BNO₂
• 分子量: 281.162
• InChiKey: CMGIUUPUDMXXLT-UHFFFAOYSA-N

物化性质

• 沸点：
  403.9±28.0 °C(Predicted)
• 密度：
  1.09

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-(2-Pyridinyl)phenylboronic acid pinacol ester
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-(2-Pyridinyl)phenylboronic acid pinacol ester
CAS number: 908350-80-1

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C17H20BNO2
Molecular weight: 281.2

---

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.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(2-吡啶基)苯硼酸频哪醇酯 在 α,α,α-三联吡啶 、 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate) 、 [(terpy)Pd(MeCN)][BF4]2 、 sodium fluoride 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 34.0h， 生成 2-(4-氟苯基)吡啶
  参考文献：
  名称：

  钯(III)催化芳基硼酸衍生物的氟化

  摘要：

  提出了一种实用的钯催化从芳基硼酸衍生物合成芳基氟化物的方法。该反应操作简单，适合多克规模的合成。反应机制的评估表明单电子转移途径，涉及已分离和表征的 Pd(III) 中间体。

  DOI：

  10.1021/ja405919z
• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以39%的产率得到4-(2-吡啶基)苯硼酸频哪醇酯
  参考文献：
  名称：

  WO2006/93466

  摘要：

  公开号：

文献信息

• Derisking the Cu-Mediated ¹⁸F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands
  作者：Nicholas J. Taylor、Enrico Emer、Sean Preshlock、Michael Schedler、Matthew Tredwell、Stefan Verhoog、Joel Mercier、Christophe Genicot、Véronique Gouverneur

  DOI：10.1021/jacs.7b03131

  日期：2017.6.21

  Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach

  用氟 18 (18F) 标记的分子用于正电子发射断层扫描，以可视化、表征和测量体内的生物过程。尽管最近在将 18F 掺入芳烃方面取得了进展，但开发通用且有效的方法来标记药物发现计划所需的放射性配体仍然是一项重大任务。这个完整的描述描述了杂环正电子发射断层扫描 (PET) 放射性配体的放射合成方法，使用铜介导的 18F 氟化芳基硼试剂与 18F 氟化物作为模型反应。该方法基于一项研究，该研究检查了药物开发中常用的杂环的存在如何影响代表性芳基硼试剂的 18F-氟化效率，以及超过 50 种（杂）芳基硼酸酯的标记。这组数据允许将这种去风险策略应用于七种结构复杂的药物相关含杂环分子的成功放射合成。
• Cleavage of C(aryl)−CH ₃ Bonds in the Absence of Directing Groups under Transition Metal Free Conditions
  作者：Peng‐Fei Dai、Xiao‐Shan Ning、Hua Wang、Xian‐Chao Cui、Jie Liu、Jian‐Ping Qu、Yan‐Biao Kang

  DOI：10.1002/anie.201901783

  日期：2019.4.8

  carbon–carbon σ‐bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site‐selective cleavage and borylation of C(aryl)−CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes

  现在，有机化学家可以选择性地和顺序地构建碳-碳σ键，而选择性裂解碳-碳σ键的方法，特别是对于未反应的碳氢化合物，仍然受到限制。通常需要通过环应变，引导基团或在羰基或氰基的存在下进行活化。在这项工作中，通过使用顺序策略C（芳基）-CH 3的位点选择性裂解和硼化在指导无基团和无过渡金属的条件下开发了键。各种芳烃的甲基被选择性裂解并被硼基取代。机理分析表明，它是通过分子间的连续分子间氧化和由自由基脱羧反应生成的涉及芳基稳定的持久性硼基自由基的瞬态芳基自由基偶联而进行的。
• AROMATIC COMPOUNDS
  申请人：Merck Patent GmbH

  公开号：US20200039903A1

  公开（公告）日：2020-02-06

  The present invention relates to aromatic compounds suitable for preparation of asymmetric polydentate ligands. The present invention further describes a process for preparing asymmetric polydentate ligands and metal complexes comprising these ligands which are suitable for use as emitters in organic electroluminescent devices.

  本发明涉及适用于制备不对称多齿配体的芳香化合物。本发明进一步描述了一种制备不对称多齿配体和包括这些配体的金属络合物的方法，这些金属络合物适用于作为有机电致发光器件中的发射体。
• 一种可捕获单线态氧的离子型磷光铱(III)配 合物及其制备方法和应用
  申请人：南京邮电大学

  公开号：CN110845544B

  公开（公告）日：2022-04-05

  本发明公开了一种可捕获单线态氧的离子型磷光铱(III)配合物，该类配合物材料由环金属配体，金属中心铱和修饰和N^N辅助配体组成，结构式为制备方法主要是1,4‑二甲基萘溴化，接着C^N配体与1,4‑二甲基萘相连，接着与铱(III)二氯桥通过配位反应制备得到配合物中间体，最后将中间体与N^N配体配位得到目标配合物；发明所述的磷光铱(III)配合物在磷光寿命成像上具有比较广泛的应用前景。
• A Pyridine–Pyridine Cross‐Coupling Reaction via Dearomatized Radical Intermediates
  作者：J. Luke Koniarczyk、Jacob W. Greenwood、Juan V. Alegre‐Requena、Robert S. Paton、Andrew McNally

  DOI：10.1002/anie.201906267

  日期：2019.10.14

  and cyanopyridines using B2 pin2 as an electron-transfer reagent. Complete regio- and cross-selectivity are observed when forming a range of valuable 2,4'-bipyridines. Phosphonium salts were found to be the only viable radical precursors in this process, and mechanistic studies indicate that the process does not proceed through a Minisci-type coupling involving a pyridyl radical. Instead, a radical-radical

  使用B2 pin2作为电子转移试剂，在吡啶基phospho盐和氰基吡啶之间开发了吡啶-吡啶偶联反应。当形成一系列有价值的2,4'-联吡啶时，观察到完全的区域选择性和交叉选择性。发现os盐是该过程中唯一可行的自由基前体，并且机理研究表明，该过程不会通过涉及吡啶基的Minisci型偶联进行。取而代之的是，硼烷基phospho吡啶基和硼基稳定的氰基吡啶基之间的自由基-自由基偶联过程解释了CC键形成步骤。