4-(苯氧基甲基)苯硼酸 | 397843-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(苯氧基甲基)苯硼酸
• 英文名称: [4-(phenoxymethyl)phenyl]boronic acid
• 英文别名: 4-(Phenoxymethyl)phenylboronic acid
• CAS: 397843-61-7
• 化学式: C₁₃H₁₃BO₃
• 分子量: 228.055
• InChiKey: IXDHTLPOOZIZJX-UHFFFAOYSA-N

物化性质

• 沸点：
  414.0±47.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P264,P280,P305+P351+P338,P337+P313
• 危险性描述：
  H319
• 储存条件：
  2-8°C，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(Phenoxymethyl)phenylboronic acid
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: 4-(Phenoxymethyl)phenylboronic acid
CAS number: 397843-61-7

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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: C13H13BO3
Molecular weight: 228.1

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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.

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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-(苯氧基甲基)苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 乙醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 10-(4-ethylphenyl)-2-(phenoxymethyl)phenanthrene
  参考文献：
  名称：

  Ag（I）催化的环异构化反应：取代的菲和萘噻吩的合成

  摘要：

  本文描述了银通过6-内挖分子内炔烃-芳烃偶联反应由邻烷基化的联芳基衍生物催化银取代的菲和萘噻吩的合成。机理研究表明，6-内-挖-环化反应是通过炔单元的初始π配位，然后在相邻的芳烃环上进行Friedel-Crafts型亲电子芳环化而进行的。X射线晶体学研究进一步支持了碳环的形成。

  DOI：

  10.1039/c7ob01646h
• 作为产物：
  描述：

  4-(溴甲基)苯硼酸 、 sodium phenoxide 在 N,N-diethanolaminomethyl polystyrene 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 N-甲基吡咯烷酮 、 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以61%的产率得到4-(苯氧基甲基)苯硼酸
  参考文献：
  名称：

  通用固相方法用于硼酸的固定化，衍生化和树脂到树脂的转移反应。

  摘要：

  含硼酸的分子广泛用于生物学，医学和合成领域。然而，这些化合物往往难以通过溶液相方法处理。在此，该问题通过用于官能化硼酸的衍生化的第一种通用固相方法的开发来解决。该方法基于使用二乙醇胺树脂锚，该锚通过避免在酯化过程中彻底去除水的需要而促进了硼酸的固定。通过在室温下在无水溶剂中简单搅拌，可以在数分钟内将多种硼酸固定在N，N-二乙醇氨基甲基聚苯乙烯（DEAM-PS，1）上。通过（1）DEAM-PS负载的对甲苯基硼酸的（1）NMR分析显示了形成具有假定的NB配位的双环二乙醇胺硼酸酯的证据。通过紫外光谱研究了DEAM-PS树脂对相同型号硼酸的水解裂解。水解和附着显示在快速达到的平衡下发生，并且需要大量过量的水（> 32当量）以实现从DEAM-PS实际定量释放硼酸。尽管它们对水和醇具有相对的敏感性，但可以用甲酰基，溴甲基，羧基或氨基官能化的DEAM-PS结合的芳基硼酸以良好或极高的收率转化成各种胺，酰

  DOI：

  10.1021/jo0106501

文献信息

• 吡咯并嘧啶类化合物作为激酶抑制剂的制备及其应用
  申请人：药雅科技(上海)有限公司

  公开号：CN115073469A

  公开（公告）日：2022-09-20

  本发明涉及一种新型Bruton's酪氨酸激酶抑制剂，该抑制剂是一类含有多芳香杂环结构的化合物，包括式(I)所示的化合物或其异构体、水合物、溶剂化物、多晶型物、药学上可接受的盐，同时公开了该类化合物的制备方法和使用这些新型化合物治疗或者预防Bruton's酪氨酸激酶相关疾病如急性淋巴细胞白血病(ALL)、慢性粒细胞白血病(CML)、套细胞淋巴瘤(MCL)、大肠癌、类风湿关节炎、抗器官移植排异、抗牛皮癣、红斑狼疮等。
• [EN] CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF<br/>[FR] MODULATEURS DE CALPAIN ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：BLADE THERAPEUTICS INC

  公开号：WO2018064119A8

  公开（公告）日：2019-04-25
• Optimization of 1,2,3,4-Tetrahydroacridin-9(10<i>H</i>)-ones as Antimalarials Utilizing Structure–Activity and Structure–Property Relationships
  作者：R. Matthew Cross、Jordany R. Maignan、Tina S. Mutka、Lisa Luong、Justin Sargent、Dennis E. Kyle、Roman Manetsch

  DOI：10.1021/jm200015a

  日期：2011.7.14

  Antimalarial activity of 1,2,3,4-tetrahydroacridin-9(10H)-ones (THAs) has been known since the 1940s and has garnered more attention with the development of the acridinedione floxacrine (1) in the 1970s and analogues thereof such as WR 243251 (2a) in the 1990s. These compounds failed just prior to clinical development because of suboptimal activity, poor solubility, and rapid induction of parasite resistance. Moreover, detailed structure-activity relationship (SAR) studies of the THA core scaffold were lacking and SPR studies were nonexistent. To improve upon initial findings, several series of 1,2,3,4-tetrahydroacridin-9(10H)-ones were synthesized and tested in a systematic fashion, examining each compound for antimalarial activity, solubility, and permeability. Furthermore, a select set of compounds was chosen for microsomal stability testing to identify physicochemical liabilities of the THA scaffold. Several potent compounds (EC50 < 100 nM) were identified to be active against the clinically relevant isolates W2 and TM90-C2B while possessing good physicochemical properties and little to no cross-resistance.
• Orally Bioavailable 6-Chloro-7-methoxy-4(1<i>H</i>)-quinolones Efficacious against Multiple Stages of <i>Plasmodium</i>
  作者：R. Matthew Cross、David L. Flanigan、Andrii Monastyrskyi、Alexis N. LaCrue、Fabián E. Sáenz、Jordany R. Maignan、Tina S. Mutka、Karen L. White、David M. Shackleford、Ian Bathurst、Frank R Fronczek、Lukasz Wojtas、Wayne C. Guida、Susan A. Charman、Jeremy N. Burrows、Dennis E. Kyle、Roman Manetsch

  DOI：10.1021/jm500942v

  日期：2014.11.13

  The continued proliferation of malaria throughout temperate and tropical regions of the world has promoted a push for more efficacious treatments to combat the disease. Unfortunately, more recent remedies such as artemisinin combination therapies have been rendered less effective due to developing parasite resistance, and new drugs are required that target the parasite in the liver to support the disease elimination efforts. Research was initiated to revisit antimalarials developed in the 1940s and 1960s that were deemed unsuitable for use as therapeutic agents as a result of poor understanding of both physicochemical properties and parasitology. Structure-activity and structure-property relationship studies were conducted to generate a set of compounds with the general 6-chloro-7-methoxy-2-methyl-4(1H)-quinolone scaffold which were substituted at the 3-position with a variety of phenyl moieties possessing various properties. Extensive physicochemical evaluation of the quinolone series was carried out to downselect the most promising 4(1H)-quinolones, 7, 62, 66, and 67, which possessed low-nanomolar EC50 values against W2 and TM90-C2B as well as improved microsomal stability. Additionally, in vivo Thompson test results using Plasmodium berghei in mice showed that these 4(1H)-quinolones were efficacious for the reduction of parasitemia at >99% after 6 days.