苯氧基苯-4-硼酸频哪醇酯 | 269410-26-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯氧基苯-4-硼酸频哪醇酯
• 英文名称: 4,4,5,5-tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane
• 英文别名: 4-phenoxyphenylboronic acid pinacol ester
• CAS: 269410-26-6
• 化学式: C₁₈H₂₁BO₃
• 分子量: 296.174
• InChiKey: SFCRPRMZQXUXOG-UHFFFAOYSA-N

物化性质

• 熔点：
  54 °C
• 沸点：
  393.2±25.0 °C(Predicted)
• 密度：
  1.09
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Phenoxyphenylboronic acid, pinacol ester
Synonyms: 4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane

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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-Phenoxyphenylboronic acid, pinacol ester
CAS number: 269410-26-6

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C18H21BO3
Molecular weight: 296.2

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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.

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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：

  苯氧基苯-4-硼酸频哪醇酯 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (R)-3-[4-氨基-3-(4-苯氧基苯基)-1H-吡唑并[3,4-D]嘧啶-1-基]哌啶-1-羧酸叔丁酯
  参考文献：
  名称：

  含有共轭联烯结构的化合物、其药物组合物和 用途

  摘要：

  本发明涉及含有共轭联烯结构的化合物、其药物组合物和用途，具体涉及通式(I)表示的化合物或其盐、其药物组合物，以及其作为BTK抑制剂和/或B细胞活化抑制剂，用于预防或治疗与B细胞活性异常和/或BTK相关的疾病的用途。所述化合物对于淋巴癌、乳腺癌、肝癌、肠癌、胃癌、肺癌和子宫颈癌等癌症细胞具有较好的致死效果，说明具有潜在的治疗相关癌症和自免疫疾病的潜力。

  公开号：

  CN107759602B
• 作为产物：
  描述：

  4-苯氧基苯酚 在 iron(II) triflate 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 甲基叔丁基醚 、 乙腈 为溶剂， 反应 23.0h， 生成 苯氧基苯-4-硼酸频哪醇酯
  参考文献：
  名称：

  通过CO键活化的铁催化Csp2-B键结构的开发和机理研究。

  摘要：

  在本文中，我们描述了通过C-O键的活化，铁催化的烯基和芳基氨基甲酸酯的硼酸酯化反应。该方案显示出高效率，广泛的底物范围以及生物相关化合物的后期硼化，因此在药物化学中提供了潜在的应用。而且，该方法能够使酚衍生物进行正交转化，并且还为合成多取代的芳烃提供了良好的机会。初步的机理研究表明，通过自由基途径的Fe II / Fe III催化循环可能与反应有关。

  DOI：

  10.1021/acs.orglett.0c01937

文献信息

• <scp>Pd‐Catalyzed Site‐Selective</scp> Borylation of Simple Arenes <i>via</i> Thianthrenation ^†
  作者：Xiao‐Yue Chen、Yu‐Hao Huang、Jian Zhou、Peng Wang

  DOI：10.1002/cjoc.202000212

  日期：2020.11

  Site‐selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd‐catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations

  简单的芳烃的位点选择性硼化通过亲电子的thththrenation / Pd催化的硼化序列实现。实现这种操作上简单的过程的关键是使用Pd催化，该催化可以耐受在thththrenation步骤中使用的溶剂和酸性条件。该方案具有温和的条件，宽泛的官能团耐受性和简单的操作方法，适用于各种药物和复杂的生物活性分子的后期功能化。
• 접합 피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 포함하는 브루톤티로신 키나제 활성 관련 질환의 예방 또는 치료용 약학적 조성물
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20180137057A

  公开（公告）日：2018-12-27

  본 발명은 접합 피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 포함하는 브루톤티로신 키나제 활성 관련 질환의 예방 또는 치료용 약학적 조성물에 관한 것이다. 본 발명에 따른 접합 피리미딘 유도체는 브루톤 티로신 키나제 또는 TMD80의 활성을 억제하는 능력이 우수하므로, 브루톤 티로신 키나제 활성과 관련된 질환, 특히 암 또는 자가면역질환을 예방 또는 치료하는데 유용하게 사용할 수 있다.

  This is the translated text in Chinese: 本发明涉及连接嘧啶衍生物，其制备方法以及包含其作为有效成分的布鲁替罗辛酪氨酸激酶活性相关疾病的预防或治疗药物组合物。根据本发明，连接嘧啶衍生物具有优越的抑制布鲁替罗辛酪氨酸激酶或TMD80活性的能力，因此可以用于预防或治疗与布鲁替罗辛酪氨酸激酶活性相关的疾病，特别是癌症或自身免疫性疾病。
• Metal-Free and Redox-Neutral Conversion of Organotrifluoroborates into Radicals Enabled by Visible Light
  作者：Wenbo Liu、Peng Liu、Leiyang Lv、Chao-Jun Li

  DOI：10.1002/anie.201807181

  日期：2018.10.8

  through an SH2 process. This strategy is enabled by using water as the solvent, visible light as the energy input, and diacetyl as the promoter in the absence of any metal catalyst or redox reagent, thereby eliminating metal waste. To demonstrate its synthetic utility, an efficient acetylation to prepare valuable aryl (alkyl) methyl ketones is described and applications to construct C−C, C−I, C−Br

  将有机硼化合物转化为相应的基团在有机化学中具有广泛的合成应用。为了实现这些转化，需要采用化学计量的各种强氧化剂如Mn（OAc）3，AgNO 3 / K 2 S 2 O 8和Cu（OAc）2，并通过单电子转移机理进行。本文确立了一种独特的策略，可通过S H从有机三氟硼酸盐生成芳基和烷基2过程。在没有任何金属催化剂或氧化还原试剂的情况下，通过使用水作为溶剂，使用可见光作为能量输入，使用二乙酰作为促进剂来启用此策略，从而消除了金属浪费。为了证明其合成用途，描述了一种有效的乙酰化反应以制备有价值的芳基（烷基）甲基酮，并且构造C-C，C-I，C-Br和C-S键的应用也是可行的。实验证据表明，三联体二乙酰是该过程的关键中间体。
• Iron‐Catalyzed Fluoroalkylation of Arylborates with Sulfone Reagents: Beyond the Limitation of Reduction Potential
  作者：Zhiqiang Wei、Wenjun Miao、Chuanfa Ni、Jinbo Hu

  DOI：10.1002/anie.202102597

  日期：2021.6.7

  alkyl–aryl coupling reaction between sulfones and arylboron compounds has remained a challenge. We report the first iron-catalyzed radical difluoroalkylation of arylborates with N-heteroaryl sulfones. The coordination between the iron catalyst and the nitrogen atom of N-heteroaryl sulfones was identified to be important in overcoming the reduction potential limitation of sulfones in the intermolecular single-electron-transfer

  砜和芳基硼化合物之间的铁催化烷基-芳基偶联反应仍然是一个挑战。我们报告了第一个铁催化的芳基硼酸酯与 N-杂芳基砜的自由基二氟烷基化。铁催化剂与 N-杂芳基砜的氮原子之间的配位被认为对于克服分子间单电子转移过程中砜的还原电位限制很重要，这使得氟烷基 N-杂芳基砜（具有相对较高的还原电位）和非氟化烷基 N-杂芳基砜（具有低还原电位）作为强大的烷基化试剂。
• Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation
  作者：Shun Wang、Hua Wang、Burkhard König

  DOI：10.1016/j.chempr.2021.04.016

  日期：2021.6

  the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive

  目前正致力于获得具有高氧化还原能力的光氧化还原催化剂。然而，将目前建立的方法应用于具有高键离解能的键的活化和具有高还原电位的基材仍然具有挑战性。在此，我们介绍了一种新的光催化策略，通过使用硫醇盐作为催化剂来活化惰性取代芳烃以进行芳基硼化。该催化体系具有很强的还原能力，可与未活化的C芳基-F、C芳基-X、C芳基-O、C芳基-N和C芳基结合-S 键用于生产性自由基硼化反应，从而扩大了可用的芳基自由基前体范围。尽管具有很高的还原能力，但该方法具有广泛的底物范围和良好的官能团耐受性。光谱研究和控制实验表明，电荷转移复合物的形成是激活底物的关键步骤。

表征谱图