[4-(烯丙氧基)苯基]硼酸 | 1117776-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: [4-(烯丙氧基)苯基]硼酸
• 中文别名: [4-（烯丙氧基）苯基]硼酸
• 英文名称: (4-(allyloxy)phenyl)boronic acid
• 英文别名: 4-Allyloxyphenylboronic acid；(4-prop-2-enoxyphenyl)boronic acid
• CAS: 1117776-68-7
• 化学式: C₉H₁₁BO₃
• mdl: MFCD11103728
• 分子量: 177.996
• InChiKey: HOFUGGFJBSCHEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Allyloxyphenylboronic 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-Allyloxyphenylboronic acid
CAS number: 1117776-68-7

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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, 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: C9H11BO3
Molecular weight: 178.0

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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-(烯丙氧基)苯基]硼酸 在 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 35.0h， 生成 和厚朴酚
  参考文献：
  名称：

  重氮与醌和邻苯二酚硼酸酯的无过渡金属的C（sp2）-C（sp2）交叉偶联。

  摘要：

  无过渡金属的C（sp 2）-C（sp 2）开发了重氮醌与邻苯二酚硼酸酯的交叉偶联反应。通过该方案，可以在温和条件下以高收率或高收率获得各种联芳基和烯基苯酚。该反应具有多种功能，可用于药物和天然产物的衍生化。该方法的合成效用通过短取代多取代的三亚苯基和三种生物活性天然产物厚朴酚，苦味素M和呋喃呋喃A的合成得到证明。机理研究和密度泛函理论（DFT）计算表明，该反应涉及到硼酸酯由单重醌卡宾构成，然后通过逐步机理进行1,2-重排。

  DOI：

  10.1002/anie.202006542
• 作为产物：
  描述：

  4-溴苯酚 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 72.0h， 生成 [4-(烯丙氧基)苯基]硼酸
  参考文献：
  名称：

  二甲基二环氧乙烷（DMDO）作为有价值的氧化剂，用于合成带有环氧化物的多官能芳族咪唑鎓单体

  摘要：

  常规有机盐代表了许多研究领域的新范例。尽管它们具有巨大的潜力，但其物理化学性质的改善仍需要对其内在结构进行化学修饰。因此，开发了一种有效的途径来制备掺入芳族环和末端环氧化物的多官能咪唑单体，这提出了真正的合成挑战。在这项工作中，我们描述了各种氧化剂的反应性，以开发出强大，清洁和强大的方法来生成环氧化盐。研究了形成环氧化物的各种反应条件，例如阳离子和抗衡离子的作用以及芳族和/或脂族连接链的影响。最后，

  DOI：

  10.1039/c7gc02372c

文献信息

• [EN] GSK-3 INHIBITORS<br/>[FR] INHIBITEURS DE GSK-3
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015069594A1

  公开（公告）日：2015-05-14

  The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds to treat disorders associated with GSK-3.

  披露通常涉及到公式I的化合物，包括它们的盐，以及使用这些化合物治疗与GSK-3相关疾病的组合物和方法。
• Cu-Catalyzed Suzuki–Miyaura reactions of primary and secondary benzyl halides with arylboronates
  作者：Yan-Yan Sun、Jun Yi、Xi Lu、Zhen-Qi Zhang、Bin Xiao、Yao Fu

  DOI：10.1039/c4cc05376a

  日期：——

  A copper-catalyzed Suzuki-Miyaura coupling of benzyl halides with arylboronates is described. Varieties of primary benzyl halides as well as more challenging secondary benzyl halides with beta hydrogens or steric hindrance could be successfully converted into the corresponding products. Thus it provides access to diarylmethanes, diarylethanes and triarylmethanes.

  描述了苄基卤化物与芳基硼酸酯的铜催化的Suzuki-Miyaura偶联。各种伯苄基卤化物以及更具挑战性的具有β氢或位阻的仲苄基卤化物都可以成功转化为相应的产品。因此，它提供了接触二芳基甲烷，二芳基乙烷和三芳基甲烷的途径。
• Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds
  作者：Xiao-Yu Lu、Chu-Ting Yang、Jing-Hui Liu、Zheng-Qi Zhang、Xi Lu、Xin Lou、Bin Xiao、Yao Fu

  DOI：10.1039/c4cc09321f

  日期：——

  A copper-catalyzed cross-coupling reaction of epoxides with arylboronates is described. This reaction is not limited to aromatic epoxides, because aliphatic epoxides are also suitable substrates. In addition, N-sulfonyl aziridines can be successfully converted into the products. This reaction provides convenient access to beta-phenethyl alcohols, which are valuable synthetic intermediates.

  描述了铜与芳基硼酸酯的铜催化的交叉偶联反应。该反应不限于芳族环氧化物，因为脂族环氧化物也是合适的底物。另外，N-磺酰基氮丙啶可以成功地转化为产物。该反应可方便地获得作为有价值的合成中间体的β-苯乙醇。
• Synthesis and herbicidal activity of phenyl-substituted benzoylpyrazoles
  作者：Thomas L Siddall、David G Ouse、Zoltan L Benko、Gail M Garvin、Johnny L Jackson、Jeffrey M McQuiston、Michael J Ricks、Thomas D Thibault、James A Turner、John C VanHeertum、Monte R Weimer

  DOI：10.1002/ps.588

  日期：2002.12

  A novel series of substituted 3-phenyl benzoylpyrazoles were prepared and tested as potential grass herbicides. The targeted materials were prepared by three newly developed synthetic routes, which allowed a comprehensive study of the SAR (structure-activity relationships) of this series. The best combination of grass weed activity (Avena fatua L, Setaria viridis (L) Beauv and Alopecurus myosuroides

  制备了一系列新颖的取代的3-苯基苯甲酰基吡唑并作为潜在的除草剂进行了测试。通过三种新开发的合成途径制备了目标材料，从而可以全面研究该系列的SAR（结构-活性关系）。在苯环的4位上具有烷氧基的情况下，草杂草活性（Avena fatua L，Setaria viridis（L）Beauv和Alopecurus myosuroides Huds）与小麦选择性的最佳组合。通过在吡唑上存在叔丁基和在苯甲酰基部分的C-2位上存在甲基，进一步增强了活性。烷氧基取代的3-苯基苯甲酰基吡唑类是一类新型的除草剂，具有潜在的控制谷物中重要杂草的效用。
• 10.1021/jacs.4c04050
  作者：Xi, Longlong、Fang, Xiaowu、Wang, Minyan、Shi, Zhuangzhi

  DOI：10.1021/jacs.4c04050

  日期：——

  In this study, we present an effective and versatile method for synthesizing a diverse range of S-chirogenic sulfinamides through catalytic asymmetric aryl addition to sulfinylamines. By utilizing a nickel complex as a catalyst, this process exhibits impressive enantioselectivity and can incorporate various arylboronic acids at the sulfur position. The resulting synthetic sulfinamides are stable and

  亚磺酰胺已广泛应用于有机合成中，对其制备的研究已有一个多世纪的历史。尽管催化方法取得了进步，但在这些分子内创建硫立构中心仍然是一个重大挑战。在这项研究中，我们提出了一种有效且通用的方法，通过催化不对称芳基加成到亚磺胺上来合成各种 S-手性亚磺酰胺。通过利用镍络合物作为催化剂，该过程表现出令人印象深刻的对映选择性，并且可以在硫位置结合各种芳基硼酸。所得的合成亚磺酰胺稳定且适应性强，可以转化为多种含硫化合物。我们的研究还结合了详细的实验和计算研究，以阐明反应机理和影响对映选择性的因素。