2-溴吡啶-4-硼酸 | 458532-94-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 2-溴吡啶-4-硼酸
• 中文别名: 2-溴吡啶-4-硼酸,95%
• 英文名称: (2-bromopyridin-4-yl)boronic acid
• 英文别名: (2-bromo-4-pyridyl)boronic acid；2-Bromopyridine-4-boronic acid
• CAS: 458532-94-0
• 化学式: C₅H₅BBrNO₂
• 分子量: 201.815
• InChiKey: DFIKFQMGZNTFLI-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  按规定使用和贮存不会分解，避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险标志：
  GHS07
• 危险性描述：
  H319
• 危险性防范说明：
  P305 + P351 + P338

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Bromopyridine-4-boronic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Bromopyridine-4-boronic acid
Ingredient name:
CAS number: 458532-94-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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, under −20◦C.
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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H5BBrNO2
Molecular weight: 201.8

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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, hydrogen bromide.

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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：

  2-溴吡啶-4-硼酸 在 copper(I) oxide 、 1,1'-双(二苯基膦)二茂铁 、 lithium hydroxide monohydrate 、 水 、 氧气 、 palladium diacetate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0~80.0 ℃ 、344.75 kPa 条件下， 反应 34.0h， 生成 4-(4-cyclopropyl-1H-imidazol-1-yl)picolinic acid
  参考文献：
  名称：

  TRICYCLIC ASK1 INHIBITORS

  摘要：

  本文提供了化合物，最好是ASK1抑制剂化合物，其组成物，以及它们的制备方法，抑制ASK1的方法以及治疗由ASK1介导的疾病的方法。

  公开号：

  US20190315767A1
• 作为产物：
  描述：

  2,4-二溴吡啶 在 正丁基锂 、 四甲基乙二胺 、 硼酸三异丙酯 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 0.5h， 以68%的产率得到2-溴吡啶-4-硼酸
  参考文献：
  名称：

  新型卤代吡啶基硼酸和酯的合成。第3部分：2或3-卤代吡啶-4-基硼酸和酯

  摘要：

  本文描述了用于合成和一般的方法的新的2-，或3-卤代吡啶-4-基硼酸和酯隔离12 - 14，18 - 20。考虑到使用n BuLi进行区域选择性的卤素金属交换或使用LDA进行定向原金属化并随后从适当的单或二卤代吡啶开始用三异丙基硼酸酯淬灭，制备这些化合物。迄今为止研究的所有底物均提供单一的区域异构硼酸或酯产物。另外，已经发现这些化合物与一系列的芳基卤化物进行了Pd催化的偶联，并授权了一种制备新吡啶库的策略。

  DOI：

  10.1016/s0040-4020(02)00416-7

文献信息

• A Highly Efficient Dimeric Manganese‐Catalyzed Selective Hydroarylation of Internal Alkynes
  作者：Yubo Pang、Gengtu Liu、Congcong Huang、Xiang‐Ai Yuan、Weipeng Li、Jin Xie

  DOI：10.1002/anie.202004950

  日期：2020.7.27

  inherent double controlled strategy of sterically hindered propargyl alcohols without the installing of external directing groups. Its synthetic robustness and practicality have been illustrated by the concise synthesis of bervastatin, a hypolipidemic drug, and late‐stage modification of complex alkynes with precise regioselectivity.

  在水存在下，在没有配体参与的空气气氛下，我们已经开发了一种通用且可预测的锰催化内部炔烃加氢芳基化反应。与其他广泛使用的过渡金属催化剂（包括钯，铑，镍或铜）相比，该反应具有独特的催化特性。简单的操作，高效和出色的官能团兼容性使该协议可用于90多种结构不同的内部炔烃，克服了炔烃的电子和空间效应的影响。其独特的区域选择性和化学选择性来自于锰基催化剂对固有的双重控制策略（受阻炔丙基醇）的固有反应性，而无需安装外部引导基团。
• 2,4,5-Trisubstituted Pyrimidines as Potent HIV-1 NNRTIs: Rational Design, Synthesis, Activity Evaluation, and Crystallographic Studies
  作者：Dongwei Kang、Francesc X. Ruiz、Yanying Sun、Da Feng、Lanlan Jing、Zhao Wang、Tao Zhang、Shenghua Gao、Lin Sun、Erik De Clercq、Christophe Pannecouque、Eddy Arnold、Peng Zhan、Xinyong Liu

  DOI：10.1021/acs.jmedchem.1c00268

  日期：2021.4.8

  There is an urgent unmet medical need for novel human immunodeficiency virus type 1 (HIV-1) inhibitors that are effective against a variety of NNRTI-resistance mutations. We report our research efforts aimed at discovering a novel chemotype of anti-HIV-1 agents with improved potency against a variety of NNRTI-resistance mutations in this paper. Structural modifications of the lead K-5a2 led to the

  对于能够有效对抗各种 NNRTI 耐药突变的新型人类免疫缺陷病毒 1 型 (HIV-1) 抑制剂，医疗需求迫切且尚未得到满足。我们在本文中报告了我们的研究工作，旨在发现一种新的抗 HIV-1 药物化学型，该药物对多种 NNRTI 耐药突变具有更高的效力。先导K-5a2的结构修饰导致了有效抑制剂16c的鉴定。与已批准的药物依曲韦林相比， 16c产生了高效的抗 HIV-1 活性并改善了耐药性。共晶结构揭示了 NNIBP 周围的水网络对于结合和抵抗抗性突变的弹性的关键作用，同时表明16c向 NNRTI 相邻位点的进一步延伸作为先导开发策略。此外， 16c表现出良好的药代动力学和安全特性，表明16c作为一种有前景的抗 HIV-1 候选药物的潜力。
• 一种芴酮衍生物及其制备和应用
  申请人：武汉尚赛光电科技有限公司

  公开号：CN109574917B

  公开（公告）日：2020-12-08

  本发明公开了一种芴酮衍生物及其制备和应用。该芴酮衍生物以芴酮为核心，通过杂环桥接受体基团从而形成一类具有新的特性的化合物，作为OLED器件发光层主体材料和电子传输材料，可显著提高器件的启动电压、发光强度、外量子效率、色度、半衰期等方面的性能，提高器件工作稳定性。
• <scp>Manganese‐Catalyzed Anti‐Markovnikov</scp> Hydroarylation of Enamides: Modular Synthesis of Arylethylamines
  作者：Yijie He、Chaoyu Du、Jian Han、Jie Han、Chengjian Zhu、Jin Xie

  DOI：10.1002/cjoc.202200202

  日期：2022.7

  construction of a rich chemical space of arylethylamine motif. In this report, a practical protocol for the synthesis of arylethylamine functionality common in pharmaceutical chemicals has been developed. It proceeds by Mn-catalyzed anti-Markovnikov hydroarylation of electron-rich enamides under mild conditions without the use of ligands. In spite of mismatched electronic effects during the manganese-mediated

  芳基乙胺骨架是许多重要的生物有机化合物中的普遍基序。一线药物发现的一项艰巨任务是在构建丰富的芳基乙胺基序化学空间的基础上，寻找结构上新的候选药物而不是阿片类药物。在本报告中，开发了一种用于合成医药化学品中常见的芳基乙胺功能的实用方案。它在温和条件下通过 Mn 催化的反马尔科夫尼科夫加氢芳基化富电子烯酰胺进行，无需使用配体。尽管在锰介导的迁移插入过程中存在不匹配的电子效应，但末端和内部烯酰胺都可以在 15 分钟内与各种芳基硼酸进行区域选择性氢化。还，β-烯基化胺的收率令人满意。该反应的合成稳健性和实用性揭示了其操作简单、反应时间短、克级可行性以及在复杂分子后期修饰中的价值。
• Rhodium-Catalyzed Chemodivergent Pyridylation of Alkynes with Pyridylboronic Acids
  作者：Huilong Zhu、Junhao Xing、Changhui Wu、Chenhong Wang、Weijun Yao、Xiaowei Dou

  DOI：10.1021/acs.orglett.2c01718

  日期：2022.7.15

  pyridylboronic acids is realized under rhodium catalysis. Chemodivergent pyridylation products, including alkenylpyridines produced via the hydropyridylation pathway and cyclopenta[c]pyridines produced via the pyridylation/cyclization pathway, were selectively produced by fine-tuning the reaction conditions. A mechanistic study revealed that 1,4-rhodium migration to the pyridine ring was involved as the key step

  炔烃与吡啶基硼酸的吡啶化反应是在铑催化下实现的。通过微调反应条件选择性地产生化学发散性吡啶化产物，包括通过氢化吡啶化途径产生的烯基吡啶和通过吡啶化/环化途径产生的环戊[ c ]吡啶。一项机理研究表明，1,4-铑迁移到吡啶环是化学发散合成的关键步骤。